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

HRID 1775308Notes

Reaction equation

HRID 1775308 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH:10]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:11][CH3:12])[C:5]([C:24]#[C:25][CH:26]([O:30][CH2:31][CH3:32])[O:27][CH2:28][CH3:29])=[CH:4][N:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:24]=[C:25]([CH:26]([O:27][CH2:28][CH3:29])[O:30][CH2:31][CH3:32])[N:8]([CH2:9][CH:10]([NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][CH3:12])[C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 89825209benzyl N-[1-[[[2-chloro-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4-yl]amino]methyl]propyl]carbamate

Product 1

HCID 89825063benzyl N-[1-[[2-chloro-6-(diethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]methyl]propyl]carbamate

Procedure

benzyl N-[1-[[2-chloro-6-(diethoxymethyl)pyrrolo[2,3-d]pyrimidin-7-yl]methyl]propyl]carbamate is synthesized by treating benzyl N-[1-[[[2-chloro-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4-yl]amino]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) (M+H) 461

Sources & evidence

ORD record
ord-d7fe023d30d7485bac3ac208cbfd1994
Source dataset
uspto-grants-2016_02
Patent number
US09260442B2

Reaction notes

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