Hydrazine hydrate (1:1) → (5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)methanamine
Reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:5]2[S:10][C:9]([CH2:11][N:12]3C(=O)C4C(=CC=CC=4)C3=O)=[N:8][C:6]=2[N:7]=1.NN.O>CO>[Cl:1][C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[C:5]2[S:10][C:9]([CH2:11][NH2:12])=[N:8][C:6]=2[N:7]=1Participants
4
Procedure
To a solution of 2-((5-chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)methyl)isoindoline-1,3-dione 58 (100 mg, 0.24 mmol) in MeOH (7 mL) was added H2N—NH2.H2O. The reaction was heated at reflux for 1 h. After cooling to room temperature the reaction was quenched with water (10 mL) and extracted with EtOAc. The combined organics were dried over Na2SO4 and concentrated in vacuo to afford (5-chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)methanamine 59.