Tert-Butylamine → HCID 295702, compound

HRID 2280747Notes

Reaction equation

HRID 2280747 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][C:16]([NH2:19])([CH3:18])[CH3:17].CCN(C(C)C)C(C)C>C(O)C>[C:16]([NH:19][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)([CH3:18])([CH3:17])[CH3:15]

Participants

5

Reactant 3

HCID 6385Tert-ButylamineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 81531Diisopropylethylamine

Product 1

HCID 295702HCID 295702, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate (3 g, 12.89 mmol), 2-methylpropan-2-amine (1.565 mL, 14.83 mmol) and DIEA (2.93 mL, 16.76 mmol) in ethanol (20 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 anhydrous magnesium sulfate, filtered and evaporated to give ethyl 4-(tert-butylamino)-2-(methylthio)pyrimidine-5-carboxylate (3.20 g, 11.86 mmol, 92% yield) as a colorless oil. MS (ESI) m/z. 269.5 [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 anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-9261017d598145909609e41feb9161a2
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

Loading…