3,3-Diethoxypropyne → Tert-butyl (1-(2-chloro-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4-ylamino)cyclopentyl)methylcarbamate

HRID 1775312Notes

Reaction equation

HRID 1775312 reaction equation
Br[C:2]1[C:3]([NH:9][C:10]([CH3:21])([CH3:20])[CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH2:22]([O:24][CH:25]([O:28][CH2:29][CH3:30])[C:26]#[CH:27])[CH3:23].ClC1N=C(NCCNC(=O)OC(C)(C)C)[C:35](C#CC(OCC)OCC)=[CH:34]N=1>>[Cl:8][C:5]1[N:4]=[C:3]([NH:9][C:10]2([CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:21][CH2:35][CH2:34][CH2:20]2)[C:2]([C:27]#[C:26][CH:25]([O:28][CH2:29][CH3:30])[O:24][CH2:22][CH3:23])=[CH:7][N:6]=1

Participants

4

Reactant 3

HCID 662853,3-DiethoxypropyneHCID 86695595tert-butyl N-[2-[[2-chloro-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4-yl]amino]ethyl]carbamateHCID 86695601tert-butyl N-[2-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]-2-methyl-propyl]carbamate

Product 1

HCID 87428398Tert-butyl (1-(2-chloro-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4-ylamino)cyclopentyl)methylcarbamate

Procedure

tert-butyl N-[[1-[[2-chloro-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4-yl]amino]cyclopentyl]methyl]carbamate is synthesized by treating tert-butyl N-[2-[(5-bromo-2-chloro-pyrimidin-4-yl)amino]-2-methyl-propyl]carbamate with 3,3-diethoxyprop-1-yne in the presence of a catalyst such as Pddba using similar experimental conditions as described for the synthesis of tert-butyl N-[2-[[2-chloro-5-(3,3-diethoxyprop-1-ynyl)pyrimidin-4yl]amino]ethyl]carbamate. LCMS (ESI) 453 (M+H).

Sources & evidence

ORD record
ord-4296109e7e124eef86e73a061cfbb7cb
Source dataset
uspto-grants-2016_02
Patent number
US09260442B2

Reaction notes

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