HCID 58166466, compound → HCID 178484255, compound

HRID 1405988Notes

Reaction equation

HRID 1405988 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[C:4](=[O:14])[N:3]=1>CN(C(OC)OC)C>[F:8][C:7]1[C:2](/[N:1]=[CH:4]/[N:5]([CH3:9])[CH3:6])=[N:3][C:4](=[O:14])[N:5]([C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[CH:6]=1

Participants

3

Reactant 1

HCID 58166466HCID 58166466, compound

Product 1

HCID 178484255HCID 178484255, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 78373Dimethylformamide dimethyl acetalSolvent

Procedure

4-Amino-5-fluoro-1-(thiophen-3-yl)pyrimidin-2(1H)-one (140 mg, 0.66 mmol) was dissolved in DMF-DMA (5 mL). The reaction mixture was stirred at reflux overnight. The residual DMF-DMA was removed in vacuo, and the residue was purified by preparative thin layer chromatography to give (E)-N′-(5-fluoro-2-oxo-1-(thiophen-3-yl)-1,2-dihydropyrimidin-4-yl)-N,N-dimethylformimidamide (75 mg, 43%) as a yellow solid: mp 211-213° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.73 (s, 1H), 8.22 (d, J=6.4 Hz, 1H), 7.75 (dd, J=3.2, 1.4 Hz, 1H), 7.60 (dd, J=5.2, 3.2 Hz, 1H), 7.34 (dd, J=5.2, 1.4 Hz, 1H), 3.26 (s, 3H), 3.13 (s, 2H); ESIMS m/z 267 ([M+H]+).

Workup

  1. temperatureat reflux overnight
  2. customThe residual DMF-DMA was removed in vacuo
  3. customthe residue was purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-e3c16535feb648bbbc55683021a6531c
Source dataset
uspto-grants-2014_12
Patent number
US08916579B2

Reaction notes

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