Diethyl Ether → 4-(3,4-Dihydro-4-oxo-2-phenyl-5-pyrimidinyl)-o-phenylene diacetate

HRID 1755848Notes

Reaction equation

HRID 1755848 reaction equation
Br.[OH:2][C:3]1[CH:4]=[C:5]([C:10]2[C:11](=[O:22])[NH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:14][CH:15]=2)[CH:6]=[CH:7][C:8]=1[OH:9].[C:23](OC(=O)C)(=[O:25])[CH3:24].[CH2:30]([O:32]CC)[CH3:31]>N1C=CC=CC=1>[C:23]([O:9][C:8]1[CH:7]=[CH:6][C:5]([C:10]2[C:11](=[O:22])[NH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:14][CH:15]=2)=[CH:4][C:3]=1[O:2][C:30](=[O:32])[CH3:31])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 199178915-(3,4-dihydroxyphenyl)-2-phenyl-4(3H)-pyrimidinone hydrobromide

Product 1

HCID 218053974-(3,4-Dihydro-4-oxo-2-phenyl-5-pyrimidinyl)-o-phenylene diacetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-(3,4-Dihydroxyphenyl)-2-phenyl-4(3H)-pyrimidinone hydrobromide (6.0 g) (21.4 mmol) are dissolved in 100 ml of pyridine and treated at room temperature while stirring with 5.2 g (51 mmol) of acetic anhydride. After 1.5 hours 200 ml of diethyl ether are added thereto and the precipitated product is filtered off. The solid is washed with diethyl ether and dried in a high vacuum at 35° C. There are obtained 7.1 g of 4-(3,4-dihydro-4-oxo-2-phenyl-5-pyrimidinyl)-o-phenylene diacetate as white crystals of m.p. 240° C.

Workup

  1. additiontreated at room temperature
  2. filtrationthe precipitated product is filtered off
  3. washThe solid is washed with diethyl ether
  4. customdried in a high vacuum at 35° C

Sources & evidence

ORD record
ord-77fa1d0af38a4b4888cb3f25bab4fc08
Source dataset
uspto-grants-1995_08
Patent number
US05438052

Reaction notes

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