Hydrazine → (S)-2-(tert-butoxycarbonyl)-1,4-dimethyl-6-oxo-hexahydropyrimidine-4-carbohydrazide

HRID 643657Notes

Reaction equation

HRID 643657 reaction equation
[C:1]([O:5][C:6]([C@H:8]1[NH:13][C:12]([CH3:18])([C:14](OC)=[O:15])[CH2:11][C:10](=[O:19])[N:9]1[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:21][NH2:22]>CCO>[C:1]([O:5][C:6]([C@H:8]1[NH:13][C:12]([CH3:18])([C:14]([NH:21][NH2:22])=[O:15])[CH2:11][C:10](=[O:19])[N:9]1[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 67304104(S)-methyl 2-(tert-butoxycarbonyl)-1,4-dimethyl-6-oxo-hexahydropyrimidine-4-carboxylate

Product 1

HCID 67303828(S)-2-(tert-butoxycarbonyl)-1,4-dimethyl-6-oxo-hexahydropyrimidine-4-carbohydrazideYield 103.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (S)-methyl 2-(tert-butoxycarbonyl)-1,4-dimethyl-6-oxo-hexahydropyrimidine-4-carboxylate (0.074 g, 0.25 mmol) in EtOH (0.5 mL) was added NH2NH2 (0.023 mL, 0.75 mmol, 3 eq) and the mixture was stirred at RT for 4 h. The mixture was concentrated in vacuo to give 0.074 g (100%) of (S)-2-(tert-butoxycarbonyl)-1,4-dimethyl-6-oxo-hexahydropyrimidine-4-carbohydrazide (CY1, R6=Me) as a yellow solid. 1H NMR (CDCl3) δ 8.95 (s, 1H), 3.11 (s, 3H), 2.28 (m, 2H), 1.50 (s, 9H), 1.47 (s, 3H).

Workup

  1. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-8152422eeb7f4dc7baea0b955db14a59
Source dataset
uspto-grants-2010_04
Patent number
US07700603B2

Reaction notes

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