Triacetoxyperiodinane → 1-(2-Chloro-7-cyclopentyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-ethanone

HRID 2189331Notes

Reaction equation

HRID 2189331 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[N:25]=[CH:26][C:27]2[C:32]([CH3:33])=[C:31]([CH:34]([OH:36])[CH3:35])[N:30]([CH:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)[C:28]=2[N:29]=1.ClC1N=CC2C=C(C(=O)C)N(C(CC)CC)C=2N=1>>[Cl:23][C:24]1[N:25]=[CH:26][C:27]2[C:32]([CH3:33])=[C:31]([C:34](=[O:36])[CH3:35])[N:30]([CH:37]3[CH2:41][CH2:40][CH2:39][CH2:38]3)[C:28]=2[N:29]=1

Participants

4

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 735546581-(2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)ethanoneHCID 866373501-(2-Chloro-7-cyclopentyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-ethanol

Product 1

HCID 866373511-(2-Chloro-7-cyclopentyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-ethanone

Procedure

1-(2-Chloro-7-cyclopentyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-ethanone is prepared by Dess-Martin periodinane oxidation of 1-(2-Chloro-7-cyclopentyl-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-6-yl)-ethanol using a procedure similar to that described for 1-[2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-ethanone in the synthesis of Example 376. [M+H]+=278.03.

Sources & evidence

ORD record
ord-59bf9ebe75b343eba0a94fcb05c03dea
Source dataset
uspto-grants-2012_12
Patent number
US08324225B2

Reaction notes

Loading…