Water → HCID 19006815, compound

HRID 1742757Notes

Reaction equation

HRID 1742757 reaction equation
[CH2:1]([SH:5])[CH:2]([CH3:4])[CH3:3].[H-].[Na+].Cl[C:9]1[N:14]=[C:13]([Cl:15])[CH:12]=[C:11]([O:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[N:10]=1.O>C1COCC1>[Cl:15][C:13]1[N:14]=[C:9]([S:5][CH2:1][CH:2]([CH3:4])[CH3:3])[N:10]=[C:11]([O:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10558Isobutyl mercaptanHCID 24758Sodium hydrideHCID 19006783HCID 19006783, compound

Product 1

HCID 19006815HCID 19006815, compoundYield 108.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
20 °C

Procedure

A solution of 6.7 ml (55.3 mmol) of isobutyl mercaptan in 40 ml of THF is added dropwise to a suspension of 2.2 g of NaH in 90 ml of THF. During this addition, the temperature is prevented from rising above 50° C. by cooling. The solution is cooled to 20° C. and added to a solution of 13.0 g of 2,4-dichloro-6-(3-methylbut-1-oxy)pyrimidine in 80 ml of THF at -10° C. When the temperature has slowly risen to 25° C., the reaction mixture is poured into 200 ml of water. Extraction three times with toluene, drying of the combined organic phases using MgSO4 and evaporation of the solvent give 17.3 g of a mixture. Separation on SiO2 (petroleum ether 80°-110° C.) gives 11.5 g (71.9% of theory) of the title product.

Workup

  1. additionDuring this addition
  2. customfrom rising above 50° C.
  3. temperatureby cooling
  4. customhas slowly risen to 25° C.
  5. extractionExtraction three times with toluene
  6. customdrying of the combined organic phases
  7. customMgSO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-2b388895f2024cf6a053b843d76f54fa
Source dataset
uspto-grants-1994_08
Patent number
US05340701

Reaction notes

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