Isopropylamine → HCID 10491237, compound

HRID 2280743Notes

Reaction equation

HRID 2280743 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.[CH3:15][CH:16]([NH2:18])[CH3:17].CCN(C(C)C)C(C)C>C(O)C>[CH:16]([NH:18][C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1)([CH3:17])[CH3:15]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 81531Diisopropylethylamine

Product 1

HCID 10491237HCID 10491237, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (10 g, 43.0 mmol), propan-2-amine (4.21 mL, 49.4 mmol) and DIEA (9.76 mL, 55.9 mmol) in ethanol (140 mL) was heated at 60° C. overnight. After cooling to room temperature, the solvent was concentrated under reduced pressure and water was added. The aqueous phase was extracted three times with ethyl acetate and the combined organic phases were dried over magnesium sulfate, filtered and evaporated to give ethyl 4-(isopropylamino)-2-(methylthio)pyrimidine-5-carboxylate (10.10 g, 39.5 mmol, 92% yield) as a colorless oil. MS (ESI) m/z 256.1 [M+1]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe solvent was concentrated under reduced pressure and water
  3. additionwas added
  4. extractionThe aqueous phase was extracted three times with ethyl acetate
  5. dry with materialthe combined organic phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-0e95d47c47ca47e487020a94ad3682b3
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

Loading…