ChemicalBook CAS DataBase List 2,4-dichloro-7-Methyl-7H-pyrrolo[2,3-d]pyriMidine

2,4-dichloro-7-Methyl-7H-pyrrolo[2,3-d]pyriMidine synthesis

6synthesis methods

Product Name:2,4-dichloro-7-Methyl-7H-pyrrolo[2,3-d]pyriMidine
CAS Number:90213-67-5
Molecular formula:C7H5Cl2N3
Molecular Weight:202.04

90213-66-4

74-88-4

2,4-dichloro-7-Methyl-7H-pyrrolo[2,3-d]pyriMidine

90213-67-5

To a suspension of sodium hydride (480 mg, 12.00 mmol, 1.10 eq., 60% dispersed in mineral oil) in tetrahydrofuran (50 mL) was slowly added dropwise a solution of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (2 g, 10.64 mmol, 1.00 eq.) in tetrahydrofuran (50 mL). The reaction mixture was stirred at 0 °C for 30 min and then iodomethane (1.66 g, 11.70 mmol, 1.10 eq.) was added dropwise at the same temperature. After addition, the reaction system was brought to room temperature and stirred overnight. Upon completion of the reaction, the reaction was quenched by the addition of water (20 mL) to the mixture and subsequently extracted with ethyl acetate. The combined organic phases were washed with saturated saline, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with ethyl acetate/petroleum ether (1:5, v/v) as eluent to afford 2.1 g (98% yield) of the title compound, 2,4-dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine, as a white solid.LC-MS (ESI, m/z): 202 [M+H]+.

90213-66-4
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74-88-4
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Yield: 98%

Reaction Conditions:

Stage #1:2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine with sodium hydride in tetrahydrofuran;acetonitrile at 0; for 0.5 h;
Stage #2:methyl iodide in tetrahydrofuran;acetonitrile at 0 - 20;

Steps:

HH.1; VV.1 Step 1: Synthesis of 2,4-dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine
To a solution of sodium hydride (480 mg, 12.00 mmol, 1.10 equiv, 60%) in tetrahydrofuran (50 mL), a solution of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (2 g, 10.64 mmol, 1.00 equiv) in tetrahydrofuran (50 mL) was slowly added.
The resulting solution was stirred at 0° C. for 30 min followed by the addition of methyl iodide (1.66 g, 11.70 mmol, 1.10 equiv) at 0° C.
The mixture was stirred at room temperature overnight.
After completion, 20 mL of water was added to the mixture and the solution was extracted with ethyl acetate and washed with brine.
The organic phase was dried over anhydrous sodium sulfate, filtered and then concentrated under vacuum.
The residue was purified by silica gel column chromatography eluting with ethyl acetate/petroleum ether (1:5) to afford 2.1 g (98%) of 2,4-dichloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidine as a white solid. LC-MS (ES, m/z): 202 [M+H]

References:

Genentech, Inc.;Blaquiere, Nicole;Castanedo, Georgette;Feng, Jianwen A.;Hu, Baihua;Staben, Steven;Yuen, Po-wai;Wu, Guosheng;Lin, Xingyu;Burch, Jason US2015/57260, 2015, A1 Location in patent:Paragraph 0436; 0437; 0588; 0589

90213-66-4
495 suppliers
$8.00/250mg

90213-67-5
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$10.00/100mg

References

84955-31-7 Synthesis

2-Amino-4-chloropyrrolo[2,3-d]pyrimidine

84955-31-7
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90213-67-5
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References

52133-67-2 Synthesis

52133-67-2
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90213-67-5
66 suppliers
$10.00/100mg

References

39929-79-8 Synthesis

39929-79-8
198 suppliers
$8.00/250mg

90213-67-5
66 suppliers
$10.00/100mg

References