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

HRID 1800697
Notes
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Reaction equation

HRID 1800697 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[C:12]([N:14]([C:16]2[N:17]=[CH:18][C:19]3[N:24]=[C:23]([NH:25][C:26](=[O:28])[CH3:27])[S:22][C:20]=3[N:21]=2)[CH3:15])[CH:11]=[CH:10][C:9]=1[F:29])(C)(C)C.C1(OC)C=CC=CC=1>FC(F)(F)C(O)=O>[NH2:7][C:8]1[CH:13]=[C:12]([N:14]([CH3:15])[C:16]2[N:17]=[CH:18][C:19]3[N:24]=[C:23]([NH:25][C:26](=[O:28])[CH3:27])[S:22][C:20]=3[N:21]=2)[CH:11]=[CH:10][C:9]=1[F:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 7519AnisoleHCID 91058342Tert-butyl(5-{[2-(acetylamino)[1,3]thiazolo[5,4-d]pyrimidin-5-yl](methyl)amino}-2-fluorophenyl)carbamate

Product 1

HCID 86646079N-{5-[(3-amino-4-fluorophenyl)(methyl)amino][1,3]thiazolo[5,4-d]pyrimidin-2-yl}acetamideYield 90%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the above-mentioned crude product of tert-butyl(5-{[2-(acetylamino)[1,3]thiazolo[5,4-d]pyrimidin-5-yl](methyl)amino}-2-fluorophenyl)carbamate and anisole (1.5 mL) in trifluoroacetic acid (15 mL) was stirred at 0° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, to the obtained residue was added saturated aqueous sodium hydrogen carbonate solution (50 mL), and the mixture was extracted with ethyl acetate/tetrahydrofuran mixture (1:1, 50 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 (638 mg, 90%) as a gray solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, to the obtained residue
  2. additionwas added saturated aqueous sodium hydrogen carbonate solution (50 mL)
  3. extractionthe mixture was extracted with ethyl acetate/tetrahydrofuran mixture (1:1, 50 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-574d5d440e734e8ba2090c5239d11d2f
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08344135B2

Reaction notes

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