Hydrazine hydrate (1:1) → (5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)methanamine

HRID 1365774Notes

Reaction equation

HRID 1365774 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]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 576854132-((5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)methyl)isoindoline-1,3-dione

Product 1

HCID 57685386(5-Chloro-7-morpholinothiazolo[4,5-d]pyrimidin-2-yl)methanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 1 h
  3. customwas quenched with water (10 mL)
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organics were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93d026191f47479fbf469d9486c6c51b
Source dataset
uspto-grants-2011_02
Patent number
US07893059B2

Reaction notes

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