tert-Butanol → Mepanipyrim

HRID 2166253Notes

Reaction equation

HRID 2166253 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([CH:15]=[C:16](Cl)[CH3:17])[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(C)(C)C.[OH-].[K+]>O>[NH:1]([C:8]1[N:13]=[C:12]([CH3:14])[CH:11]=[C:10]([C:15]#[C:16][CH3:17])[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 14797Potassium HydroxideHCID 541734932-Anilino-4-methyl-6-(2-chloropropen-1-yl)pyrimidine

Product 1

HCID 86296MepanipyrimYield 55.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

Into a 100 ml reaction flask equipped with a stirrer and a thermometer, 5.2 g (0.02 mol) of 2-anilino-4-methyl-6-(2-chloropropen-1-yl)pyrimidine and 40 ml of t-butanol were charged, and the mixture was heated to 60° C. Then, 4.49 g (0.08 mol) of potassium hydroxide powder was added thereto, and the mixture was reacted for 6 hours. After completion of the reaction, the mixture was put into water and extracted with toluene. The toluene layer was washed with water and concentrated, and then it was subjected to column chromatography to obtain 2.48 g of 2-anilino-4-methyl-6-(1-propynyl)pyrimidine as slightly yellow crystals. The yield was 55.5%.

Workup

  1. customInto a 100 ml reaction flask
  2. customequipped with a stirrer
  3. customthe mixture was reacted for 6 hours
  4. customAfter completion of the reaction
  5. extractionextracted with toluene
  6. washThe toluene layer was washed with water
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c85c46300eff440884140962bcd472fd
Source dataset
uspto-grants-1990_07
Patent number
US04943675

Reaction notes

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