Ethyl Acetate → HCID 59420736, compound

HRID 499090Notes

Reaction equation

HRID 499090 reaction equation
[CH3:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[N:13]=[C:12](Cl)[N:11]=[C:10]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]=2)[CH:3]=1.[SH:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:32])[CH2:30][CH3:31])=[CH:24][CH:23]=1.C(OCC)(=O)C>C(O)(C)(C)C>[CH3:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[N:13]=[C:12]([S:21][C:22]3[CH:23]=[CH:24][C:25]([NH:28][C:29](=[O:32])[CH2:30][CH3:31])=[CH:26][CH:27]=3)[N:11]=[C:10]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:9]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 45119426HCID 45119426, compoundHCID 59420848HCID 59420848, compound

Product 1

HCID 59420736HCID 59420736, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A suspension of Ethyl 2-(6-(5-methyl-1H-pyrazol-3-ylamino)-2-chloropyrimidin-4-yl)acetate (0.676 g, 2.29 mmol) and N-(4-mercaptophenyl)propionamide (0.415 g, 2.29 mmol) in t-butanol (10 ml) was heated under reflux overnight. Reaction mixture was then cooled to room temperature, ethyl acetate (20 ml) added causing precipitation of product. Solid was collected by filtration, washed with sat. sodium hydrogen carbonate solution, water, diethyl ether then dried by suction to leave title compound as a yellow solid (0.425 g, 43%). 1H NMR (DMSO) 1.12 (3H, t), 1.20 (3H, t), 2.00 (3H, s), 2.40 (2H, q), 3.66 (2H, s), 4.11 (2H, q), 5.05 (1H, br s), 5.30 (1H, br s), 7.53 (2H, d), 7.79 (2H, d), 10.20 (1H, s); ES+ 441.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customReaction mixture
  4. customprecipitation of product
  5. filtrationSolid was collected by filtration
  6. washwashed with sat. sodium hydrogen carbonate solution, water, diethyl ether
  7. customthen dried by suction

Sources & evidence

ORD record
ord-9c0c41e63fbd4774af6c642865390add
Source dataset
uspto-grants-2010_08
Patent number
US07767672B2

Reaction notes

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