2,4,6-Trichloropyrimidine → 2,4,6-Tris(diphenylphosphinyl)pyrimidine

HRID 1065628

Reaction equation

HRID 1065628 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4](Cl)[N:3]=1.[C:10]1([P:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:17]C)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>ClC1C=CC=CC=1Cl>[C:10]1([P:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:2]2[N:7]=[C:6]([P:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[O:17])[CH:5]=[C:4]([P:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[O:17])[N:3]=2)=[O:17])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 773782,4,6-TrichloropyrimidineHCID 77636Methoxydiphenylphosphine

Product 1

HCID 205394672,4,6-Tris(diphenylphosphinyl)pyrimidineYield 61.2%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

To a stirred, refluxing mixture of 5.00 g of 2,4,6-trichloropyrimidine in 100 ml of o-dichlorobenzene under nitrogen was added dropwise 26.00 g of methyl diphenylphosphinite. After the addition was completed, the mixture was refluxed for 6.5 hours and then allowed to stand overnight at room temperature. The next day a small amount of the solvent was removed by boiling, and the solution was allowed to stand again overnight. The next day the resulting solid was separated by filtration, washed twice with benzene and three times with hexane, recrystallized from 650 ml of toluene, and dried at 100° C./0.1 mm (13 Pa) to give 11.35 g of 2,4,6-tris(diphenylphosphinyl)pyrimidine as a white solid, mp 235°-236° C. Anal. Calcd for C40H31N2O3P3 : C, 70.59; H, 4.59; N, 4.12; P, 13.65. Found: C, 70.72; H, 4.90; N, 3.92; P, 13.61.

Workup

  1. temperatureTo a stirred, refluxing
  2. additionAfter the addition
  3. temperaturethe mixture was refluxed for 6.5 hours
  4. customThe next day a small amount of the solvent was removed
  5. waitto stand again overnight
  6. customThe next day the resulting solid was separated by filtration
  7. washwashed twice with benzene and three times with hexane
  8. customrecrystallized from 650 ml of toluene
  9. customdried at 100° C./0.1 mm (13 Pa)

Sources & evidence

ORD record
ord-17abd14d508746ad9783afbb2a7a4c1b
Source dataset
uspto-grants-1982_05
Patent number
US04330461

Linked notes

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