3-cyclopropyl-1H-pyrazol-5-amine → N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-nitro-2-phenyl-pyrimidin-4-amine

HRID 1484844Notes

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][CH: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(Cl)(Cl)Cl>[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][CH:12]=4)[N:3]=3)[CH:21]=2)[CH2:19][CH2:18]1

Participants

Conditions

Temperature: 23 °C

Procedure

To a suspension of 4-chloro-5-nitro-2-phenylpyrimidine (800 mg, 3.40 mmol, 1.0 eq) in CHCl3 (20 mL) was added 5-cyclopropyl-1H-pyrazol-3-amine (832 mg, 6.80 mmol, 2.0 eq). The reaction mixture was stirred for 6 hours at 23° C. The precipitate was filtered and recrystallized to give the desired product N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-nitro-2-phenylpyrimidin-4-amine (Compound 6) (500 mg, 45.7%). LC-MS (m/z): 323.0 [M+H]+. 1H-NMR (300 MHz, DMSO-d6): δ 0.73-0.78 (m, 2H), 0.96-1.01 (m, 2H), 1.96-2.01 (m, 1H), 6.53 (s, 1H), 7.55-7.63 (m, 3H), 8.35-8.38 (m, 2H), 9.33 (s, 1H), 10.26 (s, 1H), 12.50 (s, 1H).

Workup

filtrationThe precipitate was filtered
customrecrystallized

Sources & evidence

ORD record: ord-8bf5163b15d544e1bb67e0e5dac7a186
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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