Acetic Anhydride → HCID 15147520, compound

HRID 255712Notes

Reaction equation

HRID 255712 reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([CH3:22])[N:14]=[C:13]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:12]=2)=[CH:4][CH:3]=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>O1CCCC1>[C:29]([O:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:15]([CH3:22])[N:14]=[C:13]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:12]=2)=[CH:4][CH:3]=1)(=[O:31])[CH3:30]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 135838357HCID 135838357, compound

Product 1

HCID 15147520HCID 15147520, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1.5 g of ethyl 4-(4-hydroxy-5-nitrophenyl)-6-methyl-2-phenyl-5-pyrimidinecarboxylate and 7.5 ml of acetic anhydride in 7 ml of tetrahydrofuran was stirred for 5 hours. The reaction mixture was evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (10:1). The fractions containing the desired product were combined and concentrated in vacuo. The crystalline residue was recrystallized from diethyl ether to give ethyl 4-(4-acetoxy-5-nitrophenyl)-6-methyl-2-phenyl-5-pyrimidinecarboxylate (0.23 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. customThe residue was chromatographed on silica gel eluting with a mixture of n-hexane and ethyl acetate (10:1)
  3. additionThe fractions containing the desired product
  4. concentrationconcentrated in vacuo
  5. customThe crystalline residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-d3b71b6ece7648709ef4d4d8a312b3e3
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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