Hexane → 4,6-Bis(diphenylphosphinyl)-2-methylthiopyrimidine

HRID 1065625Notes

Reaction equation

HRID 1065625 reaction equation
Cl[C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([S:9][CH3:10])[N:3]=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.[CH3:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>ClC1C=CC=CC=1Cl>[C:11]1([P:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:2]2[CH:7]=[C:6]([P:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)([C:28]3[CH:27]=[CH:26][CH:31]=[CH:30][CH:29]=3)=[O:18])[N:5]=[C:4]([S:9][CH3:10])[N:3]=2)=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 77636MethoxydiphenylphosphineHCID 805314,6-Dichloro-2-(methylthio)pyrimidine

Product 1

HCID 205394924,6-Bis(diphenylphosphinyl)-2-methylthiopyrimidine

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

To a stirred refluxing solution of 5.00 g of 4,6-dichloro-2-methylthiopyrimidine in 150 ml of o-dichlorobenzene under nitrogen was added dropwise 15.00 g of methyl diphenylphosphinite over 35 minutes. The mixture was refluxed for 5.5 hours after the addition was completed and then allowed to cool, at which time it was added to 850 ml of n-hexane. The resulting solid was separated by filtration, washed with n-hexane, and recrystallized from 100 ml of ethanol to give 11.00 g of 4,6-bis(diphenylphosphinyl)-2-methylthiopyrimidine as white crystals, mp 221°-222° C. Anal. Calcd for C29H24N2O2P2S: C, 66.15; H, 4.59; N, 5.32. Found: C, 65.59, 65.59; H, 4.54, 4.75; N, 5.04, 5.01.

Workup

  1. temperatureThe mixture was refluxed for 5.5 hours
  2. additionafter the addition
  3. temperatureto cool, at which time it
  4. customThe resulting solid was separated by filtration
  5. washwashed with n-hexane
  6. customrecrystallized from 100 ml of ethanol

Sources & evidence

ORD record
ord-5acfeeda6de146479f464a5d602bea16
Source dataset
uspto-grants-1982_05
Patent number
US04330461

Reaction notes

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