2-Chloro-3-(4-methoxyphenyl)propanal → 6-(4-Fluorophenyl)-3-(4-methoxybenzyl)imidazo[1,2-a]pyrimidine

HRID 500114Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][C:11]([NH2:14])=[N:12][CH:13]=2)=[CH:4][CH:3]=1.Cl[CH:16]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[CH:17]=O>C(O)(CC)(C)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[N:12][C:11]3[N:10]([C:16]([CH2:19][C:20]4[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=4)=[CH:17][N:14]=3)[CH:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 5-(4-fluorophenyl)pyrimidin-2-amine (50 mg, 0.3 mmol), 2-chloro-3-(4-methoxyphenyl)propanal (52 mg, 0.26 mmol) in tert-amyl alcohol (1.0 mL) in a sealed reaction vial was heated at 130° C. for 3 hours. After cooling, the mixture was purified by preparative HPLC to afford the desired product. LCMS: (M+H)=334.0.

Workup

customin a sealed reaction
temperatureAfter cooling
customthe mixture was purified by preparative HPLC

Sources & evidence

ORD record: ord-cc7561f2aeec4985a6270737d3ff10a8
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767675B2

Reaction notes

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