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

HRID 1692751Notes

Reaction equation

HRID 1692751 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 24(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-6ab51042815b45cf9154b4f41ffafa86
Source dataset
uspto-grants-2012_04
Patent number
US08158626B2

Reaction notes

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