Methyl formate → HCID 23087998, compound

HRID 1786148Notes

Reaction equation

HRID 1786148 reaction equation
[H-].[Na+].CO[C:5](=[O:15])[CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[CH:16](OC)=O.Cl.[CH3:21][O:22][C:23](=[NH:25])[NH2:24]>CC(OC)(C)C.CO>[CH3:21][O:22][C:23]1[NH:24][C:5](=[O:15])[C:6]([NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])=[CH:16][N:25]=1

Participants

7

Reactant 4

HCID 7865Methyl formateHCID 24758Sodium hydrideHCID 637609N-Boc-glycine methyl esterHCID 3083899Carbamimidic acid, methyl ester, hydrochloride (1:1)

Product 1

HCID 23087998HCID 23087998, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 15413tert-Butyl methyl etherSolvent2×

Procedure

Under a nitrogen atmosphere, MTBE (3 ml) was added to 60% sodium hydride (0.10 g). Methyl-N-tert-butoxycarbonyl-glycinate (0.39 g, 2.05 mmol) and methyl formate (0.31 g, 5.13 mmol) were dissolved in MTBE (2 ml) in an ice bath and the solution was added dropwise over 1 hr. After overnight stirring at normal temperature, the precipitate was collected by filtration and the crystal and O-methylisourea hydrochloride (0.22 g, 2.05 mmol) were stirred overnight at 40° C. in methanol. The reaction mixture was analyzed by HPLC. As a result, 2-methoxy-6-oxo-5-tert-butoxycarbonylamino-1,6-dihydropyrimidine (0.21 g, 0.88 mmol, yield 43%) was contained.

Workup

  1. additionthe solution was added dropwise over 1 hr
  2. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-68a311cfdda04b29ba6b15d97ba6f2e8
Source dataset
uspto-grants-2009_03
Patent number
US07507738B2

Reaction notes

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