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Tetrahydrofuran → 5-Bromomethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine

HRID 4673
Notes
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Reaction equation

HRID 4673 reaction equation
P(Br)(Br)[Br:2].OC1[C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)=[N:8][CH:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:10](C)C=1C.C(=O)([O-])[O-].[K+].[K+].O1[CH2:39][CH2:38][CH2:37][CH2:36]1>C1C=CC=CC=1>[Br:2][CH2:36][C:37]1[C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=2)=[N:8][C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:10][C:38]=1[CH3:39]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 11430Potassium CarbonateHCID 24614Phosphorus tribromideHCID 704198775-Hydroxy-methyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine

Product 1

HCID 104300785-Bromomethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 241
Benzene
Solvent

Procedure

To a solution of phosphorus tribromide (16.85 g) in a mixture of benzene (150 ml) and tetrahydrofuran (150 ml) was dropwise added a solution of 5-hydroxy-methyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine (30 g) in tetrahydrofuran (150 ml) under cooling at 7°-10° C. After stirring for 4 hours at the same temperature, the reaction mixture was poured into ice-water (200 ml), adjusted to pH 9.5 with saturated potassium carbonate and extracted with ethyl acetate (300 ml). After filtering off an insolble material, the organic layer was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from diethyl ether to give 5-bromomethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine (29.08 g).

Workup

  1. temperatureunder cooling at 7°-10° C
  2. extractionextracted with ethyl acetate (300 ml)
  3. filtrationAfter filtering off an insolble material
  4. washthe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-5445957897b14e47a375be80f7ca2538
Source dataset
uspto-grants-1988_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04727073

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes