Hydrazine hydrate (1:1) → (2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanamine

HRID 2262022Notes

Reaction equation

HRID 2262022 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)=[CH:8][C:6]=2[N:7]=1.NN.O>CO>[Cl:1][C:2]1[N:3]=[C:4]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[C:5]2[S:10][C:9]([CH2:11][NH2:12])=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 595931082-((2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)isoindoline-1,3-dione

Product 1

HCID 46180727(2-Chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanamineYield 73.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2-((2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methyl)isoindoline-1,3-dione 31 (100 mg, 0.24 mmol) in MeOH (7 mL) was added H2NNH2.H2O (24 μL, 0.48 mmol). 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 (2-chloro-4-morpholinothieno[3,2-d]pyrimidin-6-yl)methanamine 27 (0.05 g, 73%). MS (Q1) 285 (M)+

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-edc65234b2e948ebb29d554f9a8a0f42
Source dataset
uspto-grants-2010_12
Patent number
US07846929B2

Reaction notes

Loading…