Choline, hydroxide → HCID 86680788, compound

HRID 2370682Notes

Reaction equation

HRID 2370682 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([N:11]([CH2:13][C:14]2[S:22][C:21]3[C:20]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[N:19][C:18]([C:29]4[CH:30]=[N:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=4)=[N:17][C:16]=3[CH:15]=2)[CH3:12])=[N:9][CH:10]=1)=[O:4].[OH-].[OH:38][CH2:39][CH2:40][N+:41]([CH3:44])([CH3:43])[CH3:42]>C(Cl)Cl.CO>[OH:38][CH2:39][CH2:40][N+:41]([CH3:44])([CH3:43])[CH3:42].[OH:1][NH:2][C:3]([C:5]1[CH:10]=[N:9][C:8]([N:11]([CH2:13][C:14]2[S:22][C:21]3[C:20]([N:23]4[CH2:28][CH2:27][O:26][CH2:25][CH2:24]4)=[N:19][C:18]([C:29]4[CH:30]=[N:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=4)=[N:17][C:16]=3[CH:15]=2)[CH3:12])=[N:7][CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 31255Choline, hydroxideHCID 54575456N-Hydroxy-2-[{[2-(6-methoxypyridin-3-yl)-4-(morpholin-4-yl)thieno[3,2-d]pyrimidin-6-yl]methyl}(methyl)amino]pyrimidine-5-carboxamide

Product 1

HCID 86680788HCID 86680788, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of Compound 1 (200 mg, 0.39 mmol) in DCM/MeOH (60 mL/12 mL) was added choline hydroxide (106 mg, 0.39 mmol, 45% in MeOH). The mixture was stirred at room temperature for 2 h and was then concentrated to remove ˜30 mL of the solvent. Ethyl acetate (60 mL) was added and the mixture was stirred at room temperature for 2 h. After a small amount of precipitation occurred, the mixture was concentrated to remove ˜40 mL of the solvent and additional ethyl acetate (60 mL) was added. The mixture was stirred at room temperature for 2 h and filtered to afford Compound 5 as a white solid (180 mg, 76%).

Workup

  1. concentrationwas then concentrated
  2. customto remove ˜30 mL of the solvent
  3. additionEthyl acetate (60 mL) was added
  4. stirringthe mixture was stirred at room temperature for 2 h
  5. customAfter a small amount of precipitation
  6. concentrationthe mixture was concentrated
  7. customto remove ˜40 mL of the solvent and additional ethyl acetate (60 mL)
  8. additionwas added
  9. stirringThe mixture was stirred at room temperature for 2 h
  10. filtrationfiltered

Sources & evidence

ORD record
ord-5e850fec2cda474f8df957c6a330a2de
Source dataset
uspto-grants-2014_04
Patent number
US08710219B2

Reaction notes

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