Diethyl Ether → 5-Cyanomethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine

HRID 255726Notes

Reaction equation

HRID 255726 reaction equation
[C-:1]#[N:2].[Na+].Br[CH2:5][C:6]1[C:7]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)=[N:8][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:11]=1[CH3:12].C(OCC)C>O.C(O)C.O1CCCC1>[C:1]([CH2:5][C:6]1[C:7]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=2)=[N:8][C:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:11]=1[CH3:12])#[N:2]

Participants

7

Reactant 3

HCID 3283Diethyl EtherHCID 8929Sodium CyanideHCID 104300785-Bromomethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine

Product 1

HCID 99967205-Cyanomethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidineYield 87.2%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of sodium cyanide (4.8 g) in water (50 ml) was added a suspension of 5-bromomethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine (30 g) in a mixture of ethanol (180 ml) and tetrahydrofuran (180 ml), and the mixture was refluxed for 2 hours. The reaction mixture was poured into a mixture of ice-water (200 ml) and diethyl ether (200 ml). The precipitate was filtered, washed with water, dried in vacuo to give 5-cyanomethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine (22.5 g).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. filtrationThe precipitate was filtered
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-5490fe87ae1947839a9efc4a0af54a6b
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

Loading…