Dimethylformamide dimethyl acetal → HCID 178484257, compound

HRID 1500022Notes

Reaction equation

HRID 1500022 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.C(OCC)C>[F:8][C:7]1[C:2]([N:1]=[CH:12][N:13]([CH3:15])[CH3:14])=[N:3][C:4]([OH:9])=[N:5][CH:6]=1

Participants

5

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 178509007HCID 178509007, compound

Product 1

HCID 178484257HCID 178484257, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a magnetically stirred solution of 4-amino-5-fluoro-pyrimidin-2-ol* (4.00 g, 31.0 mmol) in DMF (100 mL) was added N,N-dimethylformamide dimethyl acetal (4.00 g, 34.0 mmol). The mixture was stirred at room temperature for 72 h, diluted with diethyl ether (200 mL), and filtered. The solid product was washed with heptane to give the title compound (5.23 g, 92% yield) as a white solid: mp 240-243° C.; 1H NMR (300 MHz, DMSO-d6) δ 10.7 (bs, 1H), 8.59 (s, 1H), 7.7 (d, J=5.6 Hz, 1H), 3.18 (s, 3H), 3.06 (s, 3H); HPLC-MS (ESI) m/z 185 (M+H)+, 183 (M−H)−. *4-amino-5-fluoro-pyrimidin-2-ol can be purchased commercially.

Workup

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

Sources & evidence

ORD record
ord-b3dec851317349c1819a615cbd652d18
Source dataset
uspto-grants-2015_12
Patent number
US09204653B2

Reaction notes

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