Ammonia → HCID 178501495, compound

HRID 1194153Notes

Reaction equation

HRID 1194153 reaction equation
Cl.Cl.[CH3:3][O:4][C:5](=[O:14])[C@H:6]([CH2:8][C:9]1[N:13]=[CH:12][NH:11][CH:10]=1)[NH2:7].N>C(Cl)(Cl)Cl>[CH3:3][O:4][C:5](=[O:14])[C@H:6]([CH2:8][C:9]1[N:13]=[CH:12][NH:11][CH:10]=1)[NH2:7]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178419105HCID 178419105, compound

Product 1

HCID 178501495HCID 178501495, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A suspension of 12.1 g histidine methyl ester dihydrochloride in 150 mL chloroform is treated at 0° C. with excess anhydrous ammonia. The resulting suspension is filtered and the filtrate is evaporated to give histidine methyl ester as an oil. This oil is dissolved in 100 mL dichloromethane and added dropwise to a refluxing solution of 8.1 g carbonyl diimidazole in 100 mL dichloromethane. Refluxing is continued 15 min after addition is complete then the reaction mixture is concentrated until it begins to crystallize. Ethyl ether is added and the solid is collected by filtration. Recrystallization from acetonitrile gives methyl-5,6,7,8-tetrahydro-5-oxoimidazo[1,5-c]-pyrimidine-7-carboxylate; mp 159°-164° C.

Workup

  1. filtrationThe resulting suspension is filtered
  2. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-b367198a29064372b5d844180795abce
Source dataset
uspto-grants-1989_03
Patent number
US04812462

Reaction notes

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