Phosphorus tribromide → 5-(1-Bromoethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine

HRID 4677

Reaction equation

HRID 4677 reaction equation
O[CH:2]([C:4]1[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)=[N:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:9]=1[CH3:10])[CH3:3].P(Br)(Br)[Br:27]>O1CCCC1>[Br:27][CH:2]([C:4]1[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)=[N:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:9]=1[CH3:10])[CH3:3]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 201513975-(1-Hydroxyethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine

Product 1

HCID 201513945-(1-Bromoethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5-(1-hydroxyethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (1.8 g) in tetrahydrofuran (10 ml) was dropped to a solution of phosphorus tribromide (0.34 ml) in tetrahydrofuran (20 ml) under ice cooling. The reaction mixture was stirred for 5 hours at the same condition and poured into ice water and extracted with ethyl acetate. The organic layer was evaporated in vacuo. The residue was chromatographed on silicagel eluting with chloroform. The fractions containing the desired product were combined and evaporated in vacuo. The residue was crystallized from diisopropyl ether to afford 5-(1-bromoethyl)-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (0.3 g).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was evaporated in vacuo
  3. customThe residue was chromatographed on silicagel
  4. washeluting with chloroform
  5. additionThe fractions containing the desired product
  6. customevaporated in vacuo
  7. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-d873a469a1aa4c19a659d20fa347bd64
Source dataset
uspto-grants-1988_02
Patent number
US04727073

Linked notes

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