Tetrahydrofuran → 7-cyclopentyl-2-(5-formyl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide

HRID 1483068Notes

Reaction equation

HRID 1483068 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][N:24]([CH3:50])[C:25]([C:27]1[N:44]([CH:45]2[CH2:49][CH2:48][CH2:47][CH2:46]2)[C:30]2[N:31]=[C:32]([NH:35][C:36]3[CH:41]=[CH:40][C:39]([CH2:42][OH:43])=[CH:38][N:37]=3)[N:33]=[CH:34][C:29]=2[CH:28]=1)=[O:26].C1COCC1.[OH-].[Na+]>ClCCl.C(O)(C)(C)C.CCOCC>[CH3:23][N:24]([CH3:50])[C:25]([C:27]1[N:44]([CH:45]2[CH2:49][CH2:48][CH2:47][CH2:46]2)[C:30]2[N:31]=[C:32]([NH:35][C:36]3[CH:41]=[CH:40][C:39]([CH:42]=[O:43])=[CH:38][N:37]=3)[N:33]=[CH:34][C:29]=2[CH:28]=1)=[O:26]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 583154387-Cyclopentyl-2-(5-hydroxymethyl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide

Product 1

HCID 583154407-cyclopentyl-2-(5-formyl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamideYield 82%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 6386tert-ButanolSolvent

Procedure

A suspension of Dess-Martin periodinane (0.435 g, 1.06 mmol) in dichloromethane (5 ml) and tert-BuOH (0.1 ml) is stirred at rt. for 15 minutes. To this mixture is added a solution of 7-cyclopentyl-2-(5-hydroxymethyl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide (0.3 g, 0.79 mmol) in dichloromethane:THF (5 ml:7 ml) over 5 minutes. The reaction is stirred at rt. for 1 h after which ether (50 ml) and NaOH 1M (25 ml) are added. The mixture stirred vigorously for 10 minutes and then the phases are separated. The aqueous layer is back-extracted with ether (25 ml). The combined organic fractions are ished with water, brine, dried (MgSO4) filtered and the solvent evaporated to give 7-cyclopentyl-2-(5-formyl-pyridin-2-ylamino)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid dimethylamide as a white solid (0.244 g, 82%).

Workup

  1. stirringThe reaction is stirred at rt
  2. stirringThe mixture stirred vigorously for 10 minutes
  3. customthe phases are separated
  4. extractionThe aqueous layer is back-extracted with ether (25 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-64146ddf4e9646bd8f6205d72270f2f9
Source dataset
uspto-grants-2016_08
Patent number
US09416136B2

Reaction notes

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