Potassium Carbonate → HCID 13277758, compound

HRID 2296377Notes

Reaction equation

HRID 2296377 reaction equation
[CH3:1][CH:2]([C:4]1[N:9]=[CH:8][C:7]([OH:10])=[CH:6][N:5]=1)[CH3:3].C(=O)([O-])[O-].[K+].[K+].[P:17](=[S:25])(Cl)([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20].[H][H]>C(#N)C>[P:17](=[S:25])([O:10][C:7]1[CH:6]=[N:5][C:4]([CH:2]([CH3:3])[CH3:1])=[N:9][CH:8]=1)([O:21][CH2:22][CH3:23])[O:18][CH2:19][CH3:20]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 17305O,O-diethyl phosphorochloridothioate2×HCID 132777572-(Propan-2-yl)pyrimidin-5-olHCID 178418361HCID 178418361, compound2×

Product 1

HCID 13277758HCID 13277758, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 166 grams of 2-(1-methylethyl)-5-pyrimidinol, 230 grams of finely powdered potassium carbonate and 1400 ml of acetonitrile was added in a slow stream 226 grams of O,O-diethyl phosphorochloridothioate. The mixture warmed to 55°. Stirring was continued until no more O,O-diethyl phosphorochloridothioate could be detected by GLC. The solids present were removed by filtration, the filtrate concentrated under vacuum, the residue taken up in diethyl ether, the ether solution washed twice with 2% aqueous sodium hydroxide, and once with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The ether was removed under vacuum leaving a pale yellow oil having a refractive index at 25° of 1.4944. On elemental analysis the product was found to contain 45.68% carbon; 6.54% hydrogen and 9.57% nitrogen. Theoretical is 45.50% carbon; 6.60% hydrogen and 9.65% nitrogen.

Workup

  1. temperatureThe mixture warmed to 55°
  2. customThe solids present were removed by filtration
  3. concentrationthe filtrate concentrated under vacuum
  4. washthe ether solution washed twice with 2% aqueous sodium hydroxide
  5. dry with materialonce with saturated sodium chloride solution and dried over anhydrous sodium sulfate
  6. customThe ether was removed under vacuum
  7. customleaving a pale yellow oil
  8. customat 25°

Sources & evidence

ORD record
ord-4d6daf6c68df4948bd680cb57729f376
Source dataset
uspto-grants-1984_01
Patent number
US04429125

Reaction notes

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