Methoxydiphenylphosphine → 5-Bromo-4-diphenylphosphinyl-2-methylthiopyrimidine

HRID 224987

Reaction equation

HRID 224987 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.[C:11]1([P:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:18]C)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>ClC1C=CC=CC=1Cl>[Br:1][C:2]1[C:3]([P:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:18])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 77636MethoxydiphenylphosphineHCID 2658815-Bromo-4-chloro-2-(methylsulfanyl)pyrimidine

Product 1

HCID 205394705-Bromo-4-diphenylphosphinyl-2-methylthiopyrimidineYield 49.3%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

To a stirred, refluxing mixture of 3.56 g of 5-bromo-4-chloro-2-methylthiopyrimidine in 100 ml of o-dichlorobenzene under nitrogen was added dropwise 10.00 g of methyl diphenylphosphinite. After the addition was completed, the mixture was refluxed for 6 hours and then allowed to cool. Volatiles were removed from the mixture under vacuum, and the residue was recrystallized from 30 ml of 1-chlorobutane and dried at 50° C./0.1 mm (13 Pa) to give 2.97 g of 5-bromo-4-diphenylphosphinyl-2-methylthiopyrimidine (shown by formula in Claim 7) as white crystals, mp 124°-127° C. Anal. Calcd for C17H14BrN2OPS: C, 50.39; H, 3.48; N, 6.91. Found: C, 50.54; H, 3.67; N, 6.84.

Workup

  1. temperatureTo a stirred, refluxing
  2. additionAfter the addition
  3. temperaturethe mixture was refluxed for 6 hours
  4. temperatureto cool
  5. customVolatiles were removed from the mixture under vacuum
  6. customthe residue was recrystallized from 30 ml of 1-chlorobutane
  7. customdried at 50° C./0.1 mm (13 Pa)

Sources & evidence

ORD record
ord-b1dcd8c8a1f44f40af31fe94fd18ce6a
Source dataset
uspto-grants-1980_11
Patent number
US04234729

Linked notes

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