Triethylamine → n-{4-[6-Amino-5-cyano-2-(6-methylpyridin-2-ylmethylsulfanyl)-pyrimidin-4-yl]phenyl}propionamide

HRID 1172263Notes

Reaction equation

HRID 1172263 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[N:5]=[C:4]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[N:20]=2)[N:3]=1.C(N(CC)CC)C.[C:33](Cl)(=[O:36])[CH2:34][CH3:35]>C(#N)C>[NH2:1][C:2]1[N:3]=[C:4]([S:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[N:20]=2)[N:5]=[C:6]([C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:33](=[O:36])[CH2:34][CH3:35])=[CH:14][CH:15]=2)[C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 668524524-Amino-6-(4-aminophenyl)-2-(6-methylpyridin-2-ylmethylsulfanyl)-pyrimidine-5-carbonitrile

Product 1

HCID 66852043n-{4-[6-Amino-5-cyano-2-(6-methylpyridin-2-ylmethylsulfanyl)-pyrimidin-4-yl]phenyl}propionamideYield 43.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The compound of Example 8 (170 mg) and triethylamine (0.2 mL) were added to 10 mL of acetonitrile, 0.12 g of propionyl chloride was added dropwise to the solution, and then the mixture was stirred at room temperature overnight. The resulting crystal was filtrated, washed with diethyl ether, and then dried under reduced pressure to give 85 mg of N-{4-[6-amino-5-cyano-2-(6-methylpyridin-2-ylmethylsulfanyl)-pyrimidin-4-yl]phenyl}propionamide as a white powder.

Workup

  1. additionwas added dropwise to the solution
  2. filtrationThe resulting crystal was filtrated
  3. washwashed with diethyl ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-2d920055d5f9401bbf8caab204e48897
Source dataset
uspto-grants-2010_11
Patent number
US07834002B2

Reaction notes

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