2-Bromopropane → ethyl 2-chloro-5-(4,5,6,7-tetrahydro-2-isopropoxy-4-oxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate

HRID 1193893Notes

Reaction equation

HRID 1193893 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].[H-].[Na+].[CH:26](Br)([CH3:28])[CH3:27]>CN(C)P(=O)(N(C)C)N(C)C>[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]=[C:14]2[O:23][CH:26]([CH3:28])[CH3:27])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 24758Sodium hydrideHCID 21270732ethyl 2-chloro-5-(1,2,4,5,6,7-hexahydro-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate

Product 1

HCID 21270718ethyl 2-chloro-5-(4,5,6,7-tetrahydro-2-isopropoxy-4-oxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

using ethyl 2-chloro-5-(1,2,4,5,6,7-hexahydro-2,4-dioxo-3H-cyclopenta[d]pyrimidin-3-yl)-benzoate with sodium hydride and isopropyl bromide in hexamethyl-phosphoric acid triamide there is obtained ethyl 2-chloro-5-(4,5,6,7-tetrahydro-2-isopropoxy-4-oxo-3H -cyclopenta[d]pyrimidin-3-yl)-benzoate. 1H-NMR (CDCl3, 400 MHz): 7.69 ppm (d,1H), 7.54 ppm (d,1H), 7.23 ppm (q,1H), 5.30 ppm (m,1H), 4.38 ppm (q,2H), 2.79 ppm (m,4H). 2.09 ppm (m,2H), 1.38 ppm (t,3H), 1.22 ppm (d,6H).

Sources & evidence

ORD record
ord-9106fe7ddabf4031aa1dd21847731073
Source dataset
uspto-grants-1989_03
Patent number
US04812164

Reaction notes

Loading…