3-cyclopropyl-1H-pyrazol-5-amine → HCID 58169553, compound

HRID 1484871Notes

Reaction equation

HRID 1484871 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:3]=1.[CH:17]1([C:20]2[NH:24][N:23]=[C:22]([NH2:25])[CH:21]=2)[CH2:19][CH2:18]1>C(O)CCC>[CH:17]1([C:20]2[NH:24][N:23]=[C:22]([NH:25][C:2]3[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][N:5]=[C:4]([C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=4)[N:3]=3)[CH:21]=2)[CH2:19][CH2:18]1

Participants

4

Reactant 2

HCID 27580143-cyclopropyl-1H-pyrazol-5-amineHCID 58169121HCID 58169121, compound

Product 1

HCID 58169553HCID 58169553, compoundYield 77,325.297%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
90 °C

Procedure

To 4-chloro-5-nitro-2-(pyridin-2-yl)pyrimidine (1.42 g, 0.006 mmol, 1 equiv.) in BuOH (20 mL) was added 5-cyclopropyl-1H-pyrazol-3-amine (1.23 g, 0.01 mmol, 1.6 equiv.) After heating at 90° C. for 4 h. the reaction mixture was filtered to produce N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-nitro-2-(pyridin-2-yl)pyrimidin-4-amine (1.5 g, 79%). LC-MS (m/z)=324 [M+H]+; 1H NMR (400 MHz, DMSO-d6): δ0.74-0.77 (m, 2H), 0.97-1.02 (m, 2H), 1.93-2.00 (m, 1H), 7.00 (s, 1H), 7.60-7.63 (m, 1H), 8.03-8.06 (m, 1H), 8.43 (d, J=7.6 Hz, 1H), 8.84 (d, J=4.0 Hz, 1H), 9.37 (s, 1H), 10.24 (s, 1H)

Workup

  1. filtrationwas filtered

Sources & evidence

ORD record
ord-9c24f66fd858490592adce66ff3a07ab
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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