Phosphorus tribromide → [(2-Chlorophenyl)amino]-n-[5-(bromomethyl)-2-methylthiopyrimidin-4-yl]carboxamide

HRID 1280580Notes

Reaction equation

HRID 1280580 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[C:17]([CH2:18]O)=[CH:16][N:15]=[C:14]([S:20][CH3:21])[N:13]=1)=[O:10].P(Br)(Br)[Br:23]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[C:17]([CH2:18][Br:23])=[CH:16][N:15]=[C:14]([S:20][CH3:21])[N:13]=1)=[O:10]

Participants

4

Reactant 2

HCID 24614Phosphorus tribromideHCID 23381141[(2-Chlorophenyl)amino]-n-[5-(hydroxymethyl)-2-methylthiopyrimidin-4-yl]carboxamide

Product 1

HCID 23381125[(2-Chlorophenyl)amino]-n-[5-(bromomethyl)-2-methylthiopyrimidin-4-yl]carboxamideYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

[(2—Chlorophenyl)amino]-N-[5-(hydroxymethyl)-2-methylthiopyrimidin-4-yl]carboxamide (1363 g) was mixed with 8L of tetrahydrofuran and mechanical stirring begun under nitrogen. Then phosphorus tribromide (135 mL) in 800 mL tetrahydrofuran were added to the mixture over 15 minutes. Stirring was continued for 4 hours, at which time the reaction was stopped and filtered. The filter cake was washed once with tetrahydrofuran and dried overnight at 55° C. in vacuum oven to give 1360 g (71%) of [(2-chlorophenyl)amino]-N-[5-(bromomethyl)-2-methylthiopyrimidin-4-yl]carboxamide (M+1 377).

Workup

  1. stirringStirring
  2. filtrationfiltered
  3. washThe filter cake was washed once with tetrahydrofuran
  4. customdried overnight at 55° C. in vacuum oven

Sources & evidence

ORD record
ord-e1f2f59b002f42e5a8fb50fc3f32f134
Source dataset
uspto-grants-2002_09
Patent number
US06451804B1

Reaction notes

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