4-Bromo-5-iodo-2-phenylpyrimidine → N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-iodo-2-phenylpyrimidin-4-amine

HRID 1484849Notes

Reaction equation

Br[C:2]1[C:7]([I:8])=[CH:6][N:5]=[C:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]=1.[CH:15]1([C:18]2[CH:22]=[C:21]([NH2:23])[NH:20][N:19]=2)[CH2:17][CH2:16]1>CCCCO>[CH:15]1([C:18]2[NH:19][N:20]=[C:21]([NH:23][C:2]3[C:7]([I:8])=[CH:6][N:5]=[C:4]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[N:3]=3)[CH:22]=2)[CH2:17][CH2:16]1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-bromo-5-iodo-2-phenylpyrimidine (1.18 g, 3.29 mmol, 1.0 equiv.) in n-BuOH (20 mL) was added 3-cyclopropyl-1H-pyrazol-5-amine (0.811 g, 6.58 mmol, 2 equ). After heating at 90° C. for 24 hours, the reaction was filtered to afford N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-iodo-2-phenylpyrimidin-4-amine (0.85 g, 88.7%). LC-MS (m/z): 404.1 [M+H]+. 1H NMR (300 MHz, DMSO-d6): δ 0.74-0.77 (m, 2H), 0.98-1.02 (m, 2H), 1.96-2.01 (m, 1H), 6.40 (s, 2H), 7.50-7.54 (m, 3H), 8.27-8.30 (m, 2H), 8.63 (s, 1H), 8.88 (s, 2H), 12.32 (s, 1H).

Workup

filtrationthe reaction was filtered

Sources & evidence

ORD record: ord-250dbf61f6ed4bbdb283b4f5186b6682
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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