Hexane → 4,6-Bis(diphenylphosphinyl)pyrimidine

HRID 1065627Notes

Reaction equation

HRID 1065627 reaction equation
Cl[C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[C:9]1([P:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:16]C)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH3:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>ClC1C=CC=CC=1Cl>[C:9]1([P:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:2]2[CH:7]=[C:6]([P:15]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)([C:26]3[CH:25]=[CH:24][CH:29]=[CH:28][CH:27]=3)=[O:16])[N:5]=[CH:4][N:3]=2)=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 709434,6-DichloropyrimidineHCID 77636Methoxydiphenylphosphine

Product 1

HCID 205394644,6-Bis(diphenylphosphinyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

To a stirred, refluxing mixture of 5.00 g 4,6-dichloropyrimidine in 100 ml of o-dichlorobenzene under nitrogen was added dropwise 17.00 g of methyl diphenylphosphinite. After the addition was completed, the mixture was refluxed for 6.5 hours and then allowed to cool. The cooled mixture was added to 750 ml of n-hexane, and the white solid that formed was separated by filtration, washed with n-hexane, recrystallized from 150 ml of toluene, and dried at 100° C./0.1 mm (13 Pa) to give 13.64 g of 4,6-bis(diphenylphosphinyl)pyrimidine as cream-colored crystals, mp 213°-215° C. Anal. Calcd for C28H22N2O2P2 : C, 70.00; H, 4.62; N, 5.83; P, 12.89. Found: C, 69.80; H, 4.65; N, 5.65; P, 12.89.

Workup

  1. temperatureTo a stirred, refluxing
  2. additionAfter the addition
  3. temperaturethe mixture was refluxed for 6.5 hours
  4. temperatureto cool
  5. customthe white solid that formed
  6. customwas separated by filtration
  7. washwashed with n-hexane
  8. customrecrystallized from 150 ml of toluene
  9. customdried at 100° C./0.1 mm (13 Pa)

Sources & evidence

ORD record
ord-44f21ebcc3624ec091bbef0bd06fb552
Source dataset
uspto-grants-1982_05
Patent number
US04330461

Reaction notes

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