Water → Tert-butyl(3-{[2-(acetylamino)[1,3]thiazolo[5,4-d]pyrimidin-5-yl](cyclopropyl)amino}phenyl)carbamate
Reaction equation
[NH2:1][C:2]1[S:3][C:4]2[N:5]=[C:6]([N:11]([CH:26]3[CH2:28][CH2:27]3)[C:12]3[CH:13]=[C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:15]=[CH:16][CH:17]=3)[N:7]=[CH:8][C:9]=2[N:10]=1.[C:29](Cl)(=[O:31])[CH3:30].O>N1C=CC=CC=1>[C:21]([O:20][C:19](=[O:25])[NH:18][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([N:11]([C:6]2[N:7]=[CH:8][C:9]3[N:10]=[C:2]([NH:1][C:29](=[O:31])[CH3:30])[S:3][C:4]=3[N:5]=2)[CH:26]2[CH2:28][CH2:27]2)[CH:13]=1)([CH3:24])([CH3:23])[CH3:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of tert-butyl {3-[(2-amino[1,3]thiazolo[5,4-d]pyrimidin-5-yl)(cyclopropyl)amino]phenyl}carbamate (1.20 g, 3.01 mmol) in pyridine (20 mL) was added acetyl chloride (859 μL, 12.1 mmol), and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added water (60 mL), and the mixture was extracted with ethyl acetate (60 mL, 20 mL). The combined organic layer was washed with saturated brine (10 mL), and filtered through a basic silica gel pad. The filtrate was concentrated under reduced pressure to give tert-butyl(3-{[2-(acetylamino)[1,3]thiazolo[5,4-d]pyrimidin-5-yl](cyclopropyl)amino}phenyl)carbamate as a dark-purple solid. The obtained compound was used for the next reaction without further purification.
Workup
- extractionthe mixture was extracted with ethyl acetate (60 mL, 20 mL)
- washThe combined organic layer was washed with saturated brine (10 mL)
- filtrationfiltered through a basic silica gel pad
- concentrationThe filtrate was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-b1f353c2a2904e69aa88148d769beba5
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08344135B2
Reaction notes
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