Acetyl chloride → HCID 91597838, compound

HRID 1800742Notes

Reaction equation

HRID 1800742 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[N:5]=[C:6]([NH:11][C:12]3[CH:13]=[C:14]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:15]=[CH:16][C:17]=3[CH3:18])[N:7]=[CH:8][C:9]=2[N:10]=1.[C:27](Cl)(=[O:29])[CH3:28].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[C:22]([O:21][C:20](=[O:26])[NH:19][C:14]1[CH:15]=[CH:16][C:17]([CH3:18])=[C:12]([NH:11][C:6]2[N:7]=[CH:8][C:9]3[N:10]=[C:2]([NH:1][C:27](=[O:29])[CH3:28])[S:3][C:4]=3[N:5]=2)[CH:13]=1)([CH3:23])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 86646094HCID 86646094, compound

Product 1

HCID 91597838HCID 91597838, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of tert-butyl {3-[(2-amino[1,3]thiazolo[5,4-d]pyrimidin-5-yl)amino]-4-methylphenyl)carbamate (1.20 g, 3.22 mmol) in pyridine (20 mL) was added acetyl chloride (575 μL, 8.06 mmol), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution (50 mL), and the mixture was extracted with ethyl acetate (50 mL, 10 mL). The combined organic layer was washed with saturated brine (10 mL), filtered through a basic silica gel pad, and the filtrate was concentrated under reduced pressure. The obtained residue was recrystallized from ethyl acetate to give the title compound (1.31 g, 98%) as a pale-purple solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (50 mL, 10 mL)
  2. washThe combined organic layer was washed with saturated brine (10 mL)
  3. filtrationfiltered through a basic silica gel pad
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-6457bdf69d82433aa3d9143bfe2c4bbf
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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