Dimethylformamide dimethyl acetal → HCID 178484259, compound

HRID 1405977Notes

Reaction equation

HRID 1405977 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]=[C:4]([OH:9])[N:3]=1.CO[CH:12](OC)[N:13]([CH3:15])[CH3:14]>CN(C=O)C.CCOCC>[F:8][C:7]1[C:2](/[N:1]=[CH:12]/[N:13]([CH3:15])[CH3:14])=[N:3][C:4](=[O:9])[NH:5][CH:6]=1

Participants

5

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178509007HCID 178509007, compound

Product 1

HCID 178484259HCID 178484259, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a magnetically stirred solution of 4-amino-5-fluoropyrimidin-2-ol (4.00 g, 31.0 mmol) in DMF (100 mL) was added N,N-dimethylformamide dimethyl acetal (DMF-DMA; 4.00 g, 34.0 mmol). The mixture was stirred at room temperature for 72 h, diluted with Et2O (200 mL), and filtered. The solid product was washed with heptane to give (E)-N′-(5-fluoro-2-oxo-1,2-dihydropyrimidin-4-yl)-N,N-dimethylformimidamide (5.23 g, 92%) as a white solid: mp 240-243° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.7 (br s, 1H), 8.59 (s, 1H), 7.7 (d, J=5.6 Hz, 1H), 3.18 (s, 3H), 3.06 (s, 3H); ESIMS m/z 185 ([M+H]+), m/z 183 ([M−H]−).

Workup

  1. filtrationfiltered
  2. washThe solid product was washed with heptane

Sources & evidence

ORD record
ord-5f775b86f5c2416e80761ab04a69b5d0
Source dataset
uspto-grants-2014_12
Patent number
US08916579B2

Reaction notes

Loading…