Dimethylformamide dimethyl acetal → (3Z)-1-Cyclopropyl-4-(dimethylamino)-3-[2-(pyridin-4-ylamino)pyrimidin-4-yl]but-3-en-2-one
Reaction equation
[CH:1]1([CH2:4][C:5](=[O:20])[CH2:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[N:8]=2)[CH2:3][CH2:2]1.[CH3:21][N:22]([CH:24](OC)OC)[CH3:23]>>[CH:1]1([CH2:4][C:5](=[O:20])/[C:6](/[C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[N:8]=2)=[CH:21]\[N:22]([CH3:24])[CH3:23])[CH2:2][CH2:3]1Participants
3
Conditions
- Temperature
- 80 °C
Procedure
1-Cyclopropyl-3-[2-(pyridin-4-ylamino)pyrimidin-4-yl]propan-2-one (8) (269 mg, 1.003 mmol) was taken up in DMF-DMA (5.369 mL, 40.1 mmol) and stirred at 80° C. for 30 minutes. The solvent was evaporated and the residue partitioned between DCM and water. The organic layer was washed with saturated sodium bicarbonate and brine, dried with sodium sulfate, and concentrated in vacuo. The crude residue was purified by Biotage™ silica gel chromatography [1-13% MeOH in DCM with 1% triethylamine] to afford the desired product as an orange/brown foam (320 mg, 99% yield). MS (ES+): m/z=324.3 (100) [MH+2]. HPLC: tR=0.88 minute over 3 minutes. Purity: >90% [HPLC (LC/MS) at 220 nm].