Diisopropylethylamine → (S)-5-chloro-N-(3-methoxy-5-(2-methylpyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine

HRID 1410110

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1.[CH3:12][O:13][C:14]1[CH:15]=[C:16]([NH2:26])[CH:17]=[C:18]([N:20]2[CH2:24][CH2:23][CH2:22][C@@H:21]2[CH3:25])[CH:19]=1.CCN(C(C)C)C(C)C>CS(C)=O.O>[Cl:1][C:2]1[N:3]=[C:4]([NH:26][C:16]2[CH:17]=[C:18]([N:20]3[CH2:24][CH2:23][CH2:22][C@@H:21]3[CH3:25])[CH:19]=[C:14]([O:13][CH3:12])[CH:15]=2)[C:5]2[N:10]=[CH:9][S:8][C:6]=2[N:7]=1

Participants

Conditions

Temperature: 30 °C

Procedure

The mixture of 5,7-dichlorothiazolo[5,4-d]pyrimidine (200 mg, 0.97 mmol), (S)-3-methoxy-5-(2-methylpyrrolidin-1-yl)benzenamine (220 mg, 1.07 mmol) and DIPEA (150 mg, 1.17 mmol) in DMSO (50 mL) was heated to 30° C. with stirring for 16 h. The mixture was diluted with water, extracted with ethyl acetate (50 mL), combined organics washed with water (10 mL×4) then brine (10 mL×2), dried over Na2SO4 and concentrated to give the residue which was purified by column chromatography (petroleum ether:ethyl acetate=20:1) to afford (S)-5-chloro-N-(3-methoxy-5-(2-methylpyrrolidin-1-yl)phenyl)thiazolo[5,4-d]pyrimidin-7-amine (280 mg, 77%) as yellow oil. LC-MS: 376 [M+H]+, tR=1.825 min.

Workup

extractionextracted with ethyl acetate (50 mL)
washcombined organics washed with water (10 mL×4)
dry with materialbrine (10 mL×2), dried over Na2SO4
concentrationconcentrated
customto give the residue which
customwas purified by column chromatography (petroleum ether:ethyl acetate=20:1)

Sources & evidence

ORD record: ord-a9d88c5eb2e64d8387ea19e7dc7b0b4c
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921383B2

Linked notes

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