Carbamimidic acid, methyl ester, sulfate (1:1) → HCID 14855114, compound

HRID 1722406Notes

Reaction equation

[N:1]1[O:2][N:3]=[C:4]2[C:9]([CH:10]=[C:11]([C:18](=O)[CH3:19])[C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])=[CH:8][CH:7]=[CH:6][C:5]=12.C(=O)(O)[O-].[Na+].S(O)(O)(=O)=O.[CH3:31][O:32][C:33](=[NH:35])[NH2:34]>CN(C)C=O.C(OCC)(=O)C>[N:1]1[O:2][N:3]=[C:4]2[C:9]([CH:10]3[C:11]([C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])=[C:18]([CH3:19])[NH:35][C:33]([O:32][CH3:31])=[N:34]3)=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 2-[(2,1,3-benzoxadiazol-4-yl)methylene]-3-oxobutanoic acid, 1-methylethyl ester (2.04 g, 7.43 mmol), sodium bicarbonate (1.87 g, 22.3 mmol) and O-methylisourea hydrogen sulfate (1.66 g, 9.66 mmol) in dimethylformamide (7.5 ml) was heated at 65° C. (oil bath) overnight under argon. The reaction was then diluted with ethyl acetate, washed several times with water, washed with saturated sodium chloride, dried (potassium carbonate), and evaporated. The residue was flash chromatographed over Merck silica gel (400 ml) eluting with 10% ethyl acetate/dichloromethane to give 4-(2,1,3-benzoxadiazol-4-yl)-1,4-dihydro-2-methoxy-6-methyl-5-pyrimidinecarboxylic acid, 1-methylethyl ester as a dark solid (0.60 g, 25%). TLC (10% ethyl acetate/dichloromethane) single spot, Rf =0.17.

Workup

washwashed several times with water
washwashed with saturated sodium chloride
dry with materialdried (potassium carbonate)
customevaporated
customchromatographed over Merck silica gel (400 ml)
washeluting with 10% ethyl acetate/dichloromethane

Sources & evidence

ORD record: ord-38708dc2714644dd998977342efd9c2b
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04855301

Reaction notes

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