Acetic Anhydride → Ethyl 4-formamidopyrimidine-2-carboxylate

HRID 2286674Notes

Reaction equation

HRID 2286674 reaction equation
[C:1](OC(=O)C)(=[O:3])C.[NH2:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:10]=1>C(O)=O>[CH:1]([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:10]=1)=[O:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13060222Ethyl 4-aminopyrimidine-2-carboxylate

Product 1

HCID 13060170Ethyl 4-formamidopyrimidine-2-carboxylateYield 57.1%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of formic acid (100 g) and acetic anhydride (204 g) was stirred for half an hour at ambient temperature. To the solution was added ethyl 4-aminopyrimidine-2-carboxylate (30 g) and the mixture was stirred for 1.5 hours at 70° to 75° C. and then evaporated to dryness. The residue was triturated with ethanol, collected by filtration and washed with ethanol to give ethyl 4-formamidopyrimidine-2-carboxylate (20.0 g), mp 205°-206° C.

Workup

  1. stirringthe mixture was stirred for 1.5 hours at 70° to 75° C.
  2. customevaporated to dryness
  3. customThe residue was triturated with ethanol
  4. filtrationcollected by filtration
  5. washwashed with ethanol

Sources & evidence

ORD record
ord-e44a99b6ce18409ea65d697314738bf0
Source dataset
uspto-grants-1981_05
Patent number
US04267176

Reaction notes

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