Methanol → 2-Amino-5-methyloxycarbonyl-1,4,5,6-tetrahydropyrimidine hydrochloride
Reaction equation
[NH2:1][C:2]1[NH:3][CH2:4][CH:5]([C:8]([OH:10])=[O:9])[CH2:6][N:7]=1.S(Cl)([Cl:13])=O.[CH3:15]O>>[ClH:13].[NH2:1][C:2]1[NH:7][CH2:6][CH:5]([C:8]([O:10][CH3:15])=[O:9])[CH2:4][N:3]=1Participants
Procedure
2-Amino-1,4,5,6-tetrahydropyrimidine-5-carboxylic acid (0.1 g, 0.5 mmol) and thionyl chloride (0.2 mL, 1.4 mmol) were refluxed in methanol for 24 h, and then evaporated to dryness in vacuo to give 2-amino-5-methyloxycarbonyl-1,4,5,6-tetrahydropyrimidine hydrochloride. 2-Amino-5-methyloxycarbonyl-1,4,5,6-tetrahydropyrimidine hydrochloride (0.1 g, 0.6 mmol) and N,N-dimethylhydrazine 98% (0.4 mL, 5.3 mmol) were refluxed in anhydrous methanol (20 mL) for 2 h, then evaporated to dryness in vacuo to give a white residue. Recrystallization of the residue from absolute ethanol and diethyl ether gave crystals (40 mg, 58%) of 2-amino-1,4,5,6-tetrahydropyrimidine-5-carboxylic-(N,N-dimethyl)hydrazide as the hydrochloride salt: mp 192°-193° C.; 1H NMR (D2O): δ2.8 (s, 1H), 3.0 (m, 1H), 3.50 (d, 4H), 3.65 (s, 6H); MS m/z 156 (M+ of free base). Anal. (C7H16N5OCl) C, H, N.
Workup
- customevaporated to dryness in vacuo
Sources & evidence
- ORD record
- ord-db6ec7d6dd2a4b6491be96119b7a43f1
- Source dataset
- uspto-grants-1997_04
- Patent number
- US05618818
Reaction notes
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