Tetrabutylammonium Fluoride → tert-butyl N-[[1-[2-chloro-6-(diethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl]methyl]carbamate

HRID 1775313Notes

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.[CH3:30][CH2:31]CC[N+](CCCC)(CCCC)CCCC.[F-]>>[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]3([CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16])[CH2:19][CH2:31][CH2:30][CH2:20]3)[C:6]=2[N:7]=1

Participants

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride

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

Product 1

HCID 87688593tert-butyl N-[[1-[2-chloro-6-(diethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl]methyl]carbamate

Procedure

tert-butyl N-[[1-[2-chloro-6-(diethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]cyclopentyl]methyl]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[2,3d]pyrimidin-7-yl]ethyl]carbamate. LCMS (ESI) 4534 (M+H).

Sources & evidence

ORD record: ord-e63026b5503c402bbd2e7756e16ab50f
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260442B2

Reaction notes

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