Anisole → N-{5-[(3-aminophenyl)(cyclopropyl)amino][1,3]thiazolo[5,4-d]pyrimidin-2-yl}acetamide

HRID 1800718Notes

Reaction equation

HRID 1800718 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]([C:18]2[N:19]=[CH:20][C:21]3[N:26]=[C:25]([NH:27][C:28](=[O:30])[CH3:29])[S:24][C:22]=3[N:23]=2)[CH:15]2[CH2:17][CH2:16]2)[CH:9]=1)(C)(C)C.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[NH2:7][C:8]1[CH:9]=[C:10]([N:14]([CH:15]2[CH2:17][CH2:16]2)[C:18]2[N:19]=[CH:20][C:21]3[N:26]=[C:25]([NH:27][C:28](=[O:30])[CH3:29])[S:24][C:22]=3[N:23]=2)[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 7519AnisoleHCID 91398068Tert-butyl(3-{[2-(acetylamino)[1,3]thiazolo[5,4-d]pyrimidin-5-yl](cyclopropyl)amino}phenyl)carbamate

Product 1

HCID 86646086N-{5-[(3-aminophenyl)(cyclopropyl)amino][1,3]thiazolo[5,4-d]pyrimidin-2-yl}acetamideYield 80%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the above-mentioned crude product of tert-butyl(3-{[2-(acetylamino)[1,3]thiazolo[5,4-d]pyrimidin-5-yl](cyclopropyl)amino}phenyl)carbamate and anisole (1.5 mL) in trifluoroacetic acid (15 mL) was stirred at 0° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, to the obtained residue was added saturated aqueous sodium hydrogen carbonate solution (60 mL), and the mixture was extracted with ethyl acetate/tetrahydrofuran mixture (9:1, 60 mL, 20 mL). The combined organic layer was washed with saturated brine (10 mL), and dried over anhydrous sodium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with ethyl acetate to give the title compound (820 mg, 80%) as a purple solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, to the obtained residue
  2. additionwas added saturated aqueous sodium hydrogen carbonate solution (60 mL)
  3. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran mixture (9:1, 60 mL, 20 mL)
  4. washThe combined organic layer was washed with saturated brine (10 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. washThe obtained residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-df8b6525c07a4e43a19b95f958fe7347
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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