5-(1H-pyrazol-1-yl)pyrimidin-2-amine → 6-{1-[6-(1H-pyrazol-1-yl)imidazo[1,2-a]pyrimidin-3-yl]cyclopropyl}quinoline

HRID 500156Notes

Reaction equation

[N:1]1([C:6]2[CH:7]=[N:8][C:9]([NH2:12])=[N:10][CH:11]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.Cl[CH:14]([C:17]1([C:20]2[CH:21]=[C:22]3[C:27](=[CH:28][CH:29]=2)[N:26]=[CH:25][CH:24]=[CH:23]3)[CH2:19][CH2:18]1)[CH:15]=O>C(O)(C)C>[N:1]1([C:6]2[CH:7]=[N:8][C:9]3[N:10]([C:14]([C:17]4([C:20]5[CH:21]=[C:22]6[C:27](=[CH:28][CH:29]=5)[N:26]=[CH:25][CH:24]=[CH:23]6)[CH2:19][CH2:18]4)=[CH:15][N:12]=3)[CH:11]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 5-(1H-pyrazol-1-yl)pyrimidin-2-amine (0.08 g, 0.5 mmol) and chloro(1-quinolin-6-ylcyclopropyl)acetaldehyde (0.1 g, 0.5 mmol) in isopropanol (15 mL) was heated at 90° C. overnight. After cooling, the mixture was purified by RP-HPLC (pH 10) to afford the desired product. LCMS: (M+H)=353.1.

Workup

temperatureAfter cooling
customthe mixture was purified by RP-HPLC (pH 10)

Sources & evidence

ORD record: ord-be590d165e584e9e823532dc293b41b1
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767675B2

Reaction notes

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