Dimethylformamide → HCID 66973566, compound

HRID 1469118Notes

Reaction equation

HRID 1469118 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[CH:6][N:5]([S:9]([C:12]2[N:13]=[CH:14][N:15]([CH3:17])[CH:16]=2)(=[O:11])=[O:10])[C:4](=[O:18])[N:3]=1.[CH3:19][N:20]([CH3:23])[CH:21]=O.COC(OC)N(C)C>CCOCC>[F:8][C:7]1[C:2]([N:1]=[CH:19][N:20]([CH3:23])[CH3:21])=[N:3][C:4](=[O:18])[N:5]([S:9]([C:12]2[N:13]=[CH:14][N:15]([CH3:17])[CH:16]=2)(=[O:11])=[O:10])[CH:6]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 78373Dimethylformamide dimethyl acetalHCID 58138402HCID 58138402, compound

Product 1

HCID 66973566HCID 66973566, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To an 8 mL screw-cap vial was added 4-amino-5-fluoro-1-(1-methyl-1H-imidazole-4-sulfonyl)-1H-pyrimidin-2-one (80 mg, 0.3 mmol), N,N-dimethylformamide (DMF; 3 mL), and dimethylformamide dimethylacetal (DMF-DMA; 70 mg, 0.6 mmol). The mixture was shaken at room temperature for 16 h, diluted with Et2O and filtered to yield the title product as a light yellow solid (68 mg, 69%): mp 228-232° C. dec; 1H NMR (300 MHz, DMSO-d6) δ 8.67 (s, 1H), 8.25-8.21 (m, 2H), 7.82 (s, 1H), 3.73 (s, 3H), 3.24 (s, 3H), 3.13 (s, 3H); ESIMS m/z 329 ([M+H]+).

Workup

  1. customTo an 8 mL screw-cap vial
  2. filtrationfiltered

Sources & evidence

ORD record
ord-4524a571779246d98946936882cf4a44
Source dataset
uspto-grants-2015_04
Patent number
US09006259B2

Reaction notes

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