Acetic Anhydride → 2-Acetamido-4-methyl-6-benzyloxypyrimidine

HRID 614318Notes

Reaction equation

HRID 614318 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[N:14]=[C:13]([CH3:15])[CH:12]=[C:11]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1>[C:1]([NH:8][C:9]1[N:14]=[C:13]([CH3:15])[CH:12]=[C:11]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 233498922-Amino-4-methyl-6-benzyloxypyrimidine

Product 1

HCID 233499132-Acetamido-4-methyl-6-benzyloxypyrimidine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Acetic anhydride (15.3 g., 0.15 mole) is added to a stirred suspension of 2-amino-4-methyl-6-benzyloxypyrimidine (23.6 g., 0.11 mole) in 150 ml of benzene. The mixture is heated at reflux for 4 hours. It is cooled, neutralized with aqueous sodium carbonate and the benzene layer separated. The benzene solution is concentrated under vacuum to an oil from which 2-acetamido-4-methyl-6-benzyloxy-pyrimidine melting at 121°-122° C. is isolated by crystallization from hexane n-butyl chloride.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 4 hours
  3. temperatureIt is cooled
  4. customthe benzene layer separated
  5. concentrationThe benzene solution is concentrated under vacuum to an oil from which 2-acetamido-4-methyl-6-benzyloxy-pyrimidine melting at 121°-122° C.
  6. customis isolated by crystallization from hexane n-butyl chloride

Sources & evidence

ORD record
ord-bc2b91c6c4274b16904506d5dd8b9540
Source dataset
uspto-grants-1979_03
Patent number
US04144338

Reaction notes

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