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

HRID 1668541Notes

Reaction equation

HRID 1668541 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-8180ffc45e0945189c16ddeffec32c23
Source dataset
uspto-grants-2011_08
Patent number
US07989446B2

Reaction notes

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