4,6-Dichloro-2-(methylthio)pyrimidine → HCID 20539481, compound

HRID 224994Notes

Reaction equation

HRID 224994 reaction equation
[CH:1]1([P:7]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[O:8]C)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:17]1[CH:22]=[C:21](Cl)[N:20]=[C:19]([S:24][CH3:25])[N:18]=1>ClC1C=CC=CC=1Cl>[CH:1]1([P:7]([CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)([C:17]2[CH:22]=[C:21]([P:7]([CH:10]3[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15]3)([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)=[O:8])[N:20]=[C:19]([S:24][CH3:25])[N:18]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 6931439Phosphinous acid, dicyclohexyl-, methyl ester

Product 1

HCID 20539481HCID 20539481, compoundYield 5.3%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A mixture of 2.50 g of methyl dicyclohexylphosphinite and 1.00 g of 4,6-dichloro-2-methylthiopyrimidine in 20 ml of o-dichlorobenzene was refluxed under nitrogen for 6.5 hours. Volatiles were removed from the mixture under vacuum, and the resulting oily residue was recrystallized twice from cyclohexane with decolorizing charcoal treatment and dried at 100° C./0.1 mm (13 Pa) to give 0.15 g of 4,6-bis(dicyclohexylphosphinyl)-2-methylthiopyrimidine (shown by formula in Claim 11) as white crystals, mp 197°-198.5° C. Anal. Calcd for C29H48N2O2P2S: C, 63.25; H, 8.79; N, 5.07; S, 5.82. Found: C, 63.19; H, 8.81; N, 4.89; S, 6.04.

Workup

  1. temperaturewas refluxed under nitrogen for 6.5 hours
  2. customVolatiles were removed from the mixture under vacuum
  3. customthe resulting oily residue was recrystallized twice from cyclohexane with decolorizing charcoal treatment
  4. customdried at 100° C./0.1 mm (13 Pa)

Sources & evidence

ORD record
ord-d8e70429cd784a9892318e10a17d9c3b
Source dataset
uspto-grants-1980_11
Patent number
US04234729

Reaction notes

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