Formic Acid → HCID 13060169, compound

HRID 2286653Notes

Reaction equation

HRID 2286653 reaction equation
[C:1](OC(=O)C)(=[O:3])C.C(O)=O.[NH2:11][C:12]1[N:17]=[C:16]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:15]=[CH:14][N:13]=1>C(OCC)(=O)C>[CH:1]([NH:11][C:12]1[N:17]=[C:16]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[CH:15]=[CH:14][N:13]=1)=[O:3]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 11286676methyl (2-aminopyrimidinyl)acetate

Product 1

HCID 13060169HCID 13060169, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of acetic anhydride (32.7 g.) and formic acid (16.2 g.) was stirred at 50° to 60° C. for 30 minutes. The solution was added to a suspension of methyl 2-(2-aminopyrimidin-4-yl)acetate (17.93 g.) in ethyl acetate (300 ml.) at room temperature over 10 minutes, and the solution was stirred at room temperature for 3 hours. After removing the insoluble substance by filtration, water (300 ml.) was added to the filtrate, and then the mixture was adjusted to pH 7 with sodium bicarbonate. The aqueous layer was separated and extracted with ethyl acetate. The extract and the organic layer were combined, washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, treated with activated charcoal, and then concentrated under reduced pressure. The residue was triturated with diethyl ether to give methyl 2-(2-formamidopyrimidin-4-yl)acetate (14.62 g.), mp 103° to 107° C.

Workup

  1. stirringthe solution was stirred at room temperature for 3 hours
  2. customAfter removing the insoluble substance
  3. filtrationby filtration, water (300 ml.)
  4. additionwas added to the filtrate
  5. customThe aqueous layer was separated
  6. extractionextracted with ethyl acetate
  7. extractionThe extract
  8. washwashed with a saturated aqueous solution of sodium chloride
  9. dry with materialdried over magnesium sulfate
  10. additiontreated with activated charcoal
  11. concentrationconcentrated under reduced pressure
  12. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-3fa8bc8349ba489f9cb54ad42750817b
Source dataset
uspto-grants-1981_05
Patent number
US04267176

Reaction notes

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