Sodium Hydroxide → (4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(5-((diphenylmethylene)amino)pyridin-3-yl)methanone

HRID 82257Notes

Reaction equation

HRID 82257 reaction equation
[Cl:1][C:2]1[C:3]2[C:10]([CH:11]([C:13]3[CH:14]=[N:15][CH:16]=[C:17]([N:19]=[C:20]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[CH:18]=3)[OH:12])=[CH:9][N:8]([CH3:33])[C:4]=2[N:5]=[CH:6][N:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:14]=[N:15][CH:16]=[C:17]([N:19]=[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:18]=3)=[O:12])=[CH:9][N:8]([CH3:33])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 86672118(4-Chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(5-((diphenylmethylene)amino)pyridin-3-yl)methanol

Product 1

HCID 86672119(4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(5-((diphenylmethylene)amino)pyridin-3-yl)methanoneYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-chloro-7-methyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)(5-((diphenylmethylene)amino)pyridin-3-yl)methanol (Preparation 228, 11.4 g, 25 mmol) in CH2Cl2 (150 mL), Dess-Martin periodinane (15.9 g, 37 mmol) was added in portions. The reaction mixture was stirred at room temperature for 10 hours and then aqueous NaOH (30 mL) was added. The mixture was stirred for a further 0.5 hours. The mixture was then separated and the aqueous layer was exacted by CH2Cl2 (100 mL×2). The combined organic layers were concentrated and washed with ether to provide the title compound as a brown solid in 99% yield, 11 g.

Workup

  1. stirringThe mixture was stirred for a further 0.5 hours
  2. customThe mixture was then separated
  3. concentrationThe combined organic layers were concentrated
  4. washwashed with ether

Sources & evidence

ORD record
ord-0b35e63e66e446f1ba025cc8ad331e9c
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

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