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1190380-49-4

1190380-49-4 Structure

1190380-49-4 Structure
IdentificationBack Directory
[Name]

1-Tetrahydro-2H-pyran-4-yl-1H-pyrazol-4-amine
[CAS]

1190380-49-4
[Synonyms]

1-(oxan-4-yl)pyrazol-4-amine
1-(oxan-4-yl)-1H-pyrazol-4-amine
4-Amino-1-(4-tetrahydropyranyl)pyrazole
1-Tetrahydro-2H-pyran-4-yl-1H-pyrazol-4-amine
1H-Pyrazol-4-amine, 1-(tetrahydro-2H-pyran-4-yl)-
4-Amino-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole, 4-(4-Amino-1H-pyrazol-1-yl)tetrahydro-2H-pyran
[Molecular Formula]

C8H13N3O
[MDL Number]

MFCD11505007
[MOL File]

1190380-49-4.mol
[Molecular Weight]

167.21
Chemical PropertiesBack Directory
[Boiling point ]

355.0±32.0 °C(Predicted)
[density ]

1.35±0.1 g/cm3(Predicted)
[storage temp. ]

under inert gas (nitrogen or Argon) at 2–8 °C
[form ]

solid
[pka]

4.12±0.19(Predicted)
[color ]

Brown
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
[HS Code ]

2933199090
Hazard InformationBack Directory
[Uses]

1-(Tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-amine is used in the synthesis of Tyk2 inhibitors as well as in the preparation of pyrimidines as GCN2 inhibitors.
[Synthesis]

4-Nitro-1-(tetrahydro-2H-pyran-4-yl-1H-pyrazole

1190380-50-7

1-Tetrahydro-2H-pyran-4-yl-1H-pyrazol-4-amine

1190380-49-4

4-Nitro-1-(tetrahydropyran-4-yl)-1H-pyrazole (1.59 g, 8.07 mmol) was used as the starting material and mixed with 10% palladium/carbon catalyst in ethanol (30 mL). The reaction mixture was stirred overnight under hydrogen atmosphere. Upon completion of the reaction, the catalyst was removed by filtration through diatomaceous earth and the filtrate was subsequently concentrated to afford the target compound 1-tetrahydro-2H-pyran-4-yl-1H-pyrazol-4-amine as a purple solid (1.33 g, 98% yield). The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 1.76-1.94 (m, 4H), 3.29-3.48 (m, 2H), 3.80 (br.s, 2H), 3.84-4.00 (m, 2H), 4.16 (tt, J = 10.42, 5.38 Hz, 1H), 6.90 (s, 1H), and 7.06 (s, 1H); mass spectrum (ES + APCI+): m/z 168 [M+H]+.

[References]

[1] Patent: WO2009/122180, 2009, A1. Location in patent: Page/Page column 111-112
[2] Patent: WO2009/155565, 2009, A1. Location in patent: Page/Page column 153
[3] Patent: WO2009/155551, 2009, A1. Location in patent: Page/Page column 116
[4] Patent: US2010/317643, 2010, A1. Location in patent: Page/Page column 98
[5] Patent: US2015/336982, 2015, A1. Location in patent: Paragraph 0285; 0287
Spectrum DetailBack Directory
[Spectrum Detail]

1-Tetrahydro-2H-pyran-4-yl-1H-pyrazol-4-amine(1190380-49-4)1HNMR
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