Ethyl 4-(2-hydroxy-5-nitrophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate → Ethyl 3-acetyl-1,2,3,4-tetrahydro-4-(2-acetoxy-5-nitrophenyl)-6-methyl-2-oxo-5-pyrimidine carboxylate

HRID 64590Notes

Reaction equation

HRID 64590 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH:11]1[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([CH3:22])[NH:14][C:13](=[O:23])[NH:12]1>C(OC(=O)C)(=O)C>[C:2]([N:12]1[CH:11]([C:3]2[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=2[O:1][C:17](=[O:18])[CH3:16])[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([CH3:22])[NH:14][C:13]1=[O:23])(=[O:1])[CH3:3]

Participants

3

Reactant 1

HCID 3097575Ethyl 4-(2-hydroxy-5-nitrophenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

Product 1

HCID 20236390Ethyl 3-acetyl-1,2,3,4-tetrahydro-4-(2-acetoxy-5-nitrophenyl)-6-methyl-2-oxo-5-pyrimidine carboxylate

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A suspension of ethyl 1,2,3,4-tetrahydro-4-(2-hydroxy-5-nitrophenyl)-6-methyl-2-oxo-5-pyrimidine carboxylate (1.00 g, 31.0 mmol) in acetic anhydride (25 mL) was heated to reflux for 2 hours. The reaction mixture was cooled and the excess acetic anhydride was removed in vacuo to afford the desired product as a tan solid which was used in the next reaction without purification.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. temperatureThe reaction mixture was cooled
  4. customthe excess acetic anhydride was removed in vacuo

Sources & evidence

ORD record
ord-3ee6384d46a24b7b903d9bad2c485252
Source dataset
uspto-grants-1986_09
Patent number
US04609494

Reaction notes

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