Propargyl bromide → ethyl 2-chloro-5-{1,2,4,5,6,7-hexahydro-1-(2-propynyl)-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl}-benzoate

HRID 1252903Notes

Reaction equation

[Cl:1][C:2]1[CH:12]=[CH:11][C:10]([N:13]2[C:18](=[O:19])[C:17]3[CH2:20][CH2:21][CH2:22][C:16]=3[NH:15][C:14]2=[O:23])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].Br[CH2:25][C:26]#[CH:27]>>[Cl:1][C:2]1[CH:12]=[CH:11][C:10]([N:13]2[C:18](=[O:19])[C:17]3[CH2:20][CH2:21][CH2:22][C:16]=3[N:15]([CH2:27][C:26]#[CH:25])[C:14]2=[O:23])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

Reactant 2

HCID 7842Propargyl bromide

HCID 21270732ethyl 2-chloro-5-(1,2,4,5,6,7-hexahydro-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate

Product 1

HCID 20130663ethyl 2-chloro-5-{1,2,4,5,6,7-hexahydro-1-(2-propynyl)-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl}-benzoate

Procedure

using ethyl 2-chloro-5-(1,2,4,5,6,7-hexahydro-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate and 3-bromo-1-propyne there is obtained ethyl 2-chloro-5-{1,2,4,5,6,7-hexahydro-1-(2-propynyl)-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl}-benzoate, m.p. 121°-123° C.,

Sources & evidence

ORD record: ord-f4afb545a2bb4fdb974473a7180d0c14
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04746352

Reaction notes

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