Tetrabutylammonium Fluoride → tert-butyl N-[2-[2-chloro-6-(diethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]-2-methyl-propyl]carbamate

HRID 1775305Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9]([CH3:20])([CH3:19])[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[C:5]([C:21]#[C:22][CH:23]([O:27][CH2:28][CH3:29])[O:24][CH2:25][CH3:26])=[CH:4][N:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].ClC1N=CC2C=C(C(OCC)OCC)N(CCNC(=O)OC(C)(C)C)C=2N=1>>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:21]=[C:22]([CH:23]([O:24][CH2:25][CH3:26])[O:27][CH2:28][CH3:29])[N:8]([C:9]([CH3:19])([CH3:20])[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16])[C:6]=2[N:7]=1

Participants

Reactant 3

HCID 2724141Tetrabutylammonium Fluoride

HCID 87428127Tert-butyl 2-(2-chloro-6-(diethoxymethyl)-7h-pyrrolo[2,3-d]pyrimidin-7-yl)ethylcarbamate

HCID 89789736tert-butyl N-[2-[[2-chloro-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4-yl]amino]-2-methyl-propyl]carbamate

Product 1

HCID 89825096tert-butyl N-[2-[2-chloro-6-(diethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]-2-methyl-propyl]carbamate

Procedure

tert-butyl N-[2-[2-chloro-6-(diethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]-2-methyl-propyl]carbamate is synthesized by treating tert-butyl N-[2-[[2-chloro-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4-yl]amino]-2-methyl-propyl]carbamate with TBAF using similar experimental conditions as described for the synthesis tert-butyl N-[2-[2-chloro-6-(diethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]ethyl]carbamate. LCMS (ESI) (M+H) 427

Sources & evidence

ORD record: ord-0a921415d9e842368f89187745bcc2cc
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260442B2

Reaction notes

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