Dimethylformamide dimethyl acetal → HCID 178484257, compound

HRID 705577Notes

Reaction equation

HRID 705577 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-cd99633246f34641b2ccb0869fc18718
Source dataset
uspto-grants-2015_11
Patent number
US09174970B2

Reaction notes

Loading…