ChemicalBook CAS DataBase List 4-Pyrimidinamine, 5-methoxy- (9CI)

4-Pyrimidinamine, 5-methoxy- (9CI) synthesis

5synthesis methods

Product Name:4-Pyrimidinamine, 5-methoxy- (9CI)
CAS Number:695-86-3
Molecular formula:C5H7N3O
Molecular Weight:125.13

Pyrimidine, 4-chloro-5-methoxy- (6CI,7CI,8CI,9CI)

695-85-2

695-86-3

General procedure for the synthesis of 4-amino-5-methoxypyrimidines from 4-chloro-5-methoxypyrimidines: 4-chloro-5-methoxypyrimidines (I-89) (40 g, 280 mmol) was suspended in NH3(g)/EtOH (4 M, 2000 mL), the suspension was transferred to an autoclave, and the reaction was stirred for 12 hours at 130 °C. The progress of the reaction was monitored by TLC (unfolding agent: CH2Cl2/MeOH = 10:1) and after confirming the completion of the reaction, the reaction mixture was cooled to room temperature. Subsequently, the mixture was concentrated under vacuum to obtain the residue. CH2Cl2 (100 mL) was added to the residue and stirred at room temperature for 30 minutes. The reaction mixture was filtered to remove the NH4Cl salt and the filtrate was concentrated under vacuum to give the crude product. The crude product was stirred with a solvent mixture of EtOAc/CH2Cl2 (50 mL, 4:1) for 30 min, filtered and concentrated in vacuum to give the final 4-amino-5-methoxypyrimidine (I-90) (30 g, 87% yield) as a yellow solid. The structure of the product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 8.01 (s, 1H), 7.81 (s, 1H), 6.75 (br.s., 2H), 3.81 (s, 3H).

695-85-2 Synthesis

695-85-2
106 suppliers
$29.00/100mg

695-86-3
73 suppliers
$33.00/250mg

Yield: 87%

Reaction Conditions:

with ammonia in ethanol at 130; for 12 h;Autoclave;

Steps:

Step 4 - Synthesis of 4-amino-5-methoxypyrimidine (I-90)
A suspension of 4-chloro-5-methoxypyrimidine (I-89) (40 g, 280 mmol) in NH3 (g)/EtOH (4 M, 2000 mL) was poured into an autoclave at room temperature and stirred at 130 °C for 12 hr. TLC (CH2CI2/MeOH = 10:1 ) showed the reaction was complete. The mixture was cooled to room temperature and concentrated in vacuo to give a residue, to which was added CH2CI2 (100 mL) and the resulting mixture was stirred at room temperature for 30 min. The resulting suspension was filtered to remove NH4CI salt, and the filtrate was concentrated in vacuo to give the crude product. The crude product was stirred in a mixed solvent of EtOAc/CH2CI2 (50 mL, 4:1 ) for 30 min, filtered and concentrated in vacuo to obtain 4-amino-5-methoxypyrimidine (I-90) (30 g, 87%) as a yellow solid. 1H NMR (400 MHz, DMSO-c/6) 8 ppm 8.01 (s, 1 H), 7.81 (s, 1 H), 6.75 (br. s., 2 H), 3.81 (s, 3 H).

References:

PFIZER INC.;JOHNSON, Ted William;RICHARDSON, Paul Francis;COLLINS, Michael Raymond;RICHTER, Daniel Tyler;BURKE, Benjamin Joseph;GAJIWALA, Ketan;NINKOVIC, Sacha;LINTON, Maria Angelica;LE, Phuong Thi Quy;HOFFMAN, Jacqui Elizabeth WO2016/97918, 2016, A1 Location in patent:Page/Page column 80

5018-41-7 Synthesis

5018-41-7
147 suppliers
$39.00/100mg

695-86-3
73 suppliers
$33.00/250mg

References

31458-33-0 Synthesis

Pyrimidine, 5-methoxy- (6CI,7CI,8CI,9CI)

31458-33-0
95 suppliers
$26.00/100mg

695-86-3
73 suppliers
$33.00/250mg

References

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
0 suppliers
inquiry

695-86-3
73 suppliers
$33.00/250mg

References

695-87-4 Synthesis

695-87-4
47 suppliers
$60.00/100mg

695-86-3
73 suppliers
$33.00/250mg

References