Methyl 5-(2-bromoacetyl)-2-hydroxybenzoate → Methyl 5-(5-chloro-2-oxopyrimidin-1-yl)acetylsalicylate

HRID 980170

Reaction equation

HRID 980170 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[NH:7][CH:8]=1.Br[CH2:11][C:12]([C:14]1[CH:23]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[C:17]([OH:24])=[CH:16][CH:15]=1)=[O:13]>C(N(CC)CC)C.C(O)C>[Cl:2][C:3]1[CH:4]=[N:5][C:6](=[O:9])[N:7]([CH2:11][C:12]([C:14]2[CH:23]=[C:18]([C:19]([O:21][CH3:22])=[O:20])[C:17]([OH:24])=[CH:16][CH:15]=2)=[O:13])[CH:8]=1

Participants

5

Reactant 2

HCID 11601501Methyl 5-(2-bromoacetyl)-2-hydroxybenzoateHCID 126485235-Chloropyrimidin-2-ol hydrochloride

Product 1

HCID 12795552Methyl 5-(5-chloro-2-oxopyrimidin-1-yl)acetylsalicylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 5-chloropyrimidin-2-one hydrochloride (508 mg) and methyl 5-bromoacetylsalicylate (827 mg) in triethylamine (1 ml) and ethanol (20 ml) was stirred at ambient temperature for 13/4 hours, by which time a precipitate had formed. This suspension was chilled in ice, and the collected solid was crystallised from chloroform-ethanol to give the title pyrimidinone: yield 442 mg: m.p. 203°-204° dec: λmaxEtOH 228.5 nm (ε 40720), 269.5 nm (ε 16930), 312.5 nm (ε 6320).

Workup

  1. customby which time a precipitate had formed
  2. temperatureThis suspension was chilled in ice
  3. customthe collected solid was crystallised from chloroform-ethanol

Sources & evidence

ORD record
ord-b7e772985ec74490bbde9a2c4ef6b3cc
Source dataset
uspto-grants-1987_01
Patent number
US04636509

Linked notes

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