Water → 7'-Chloro-1'-(2-isopropoxyethyl)-spiro[cyclopentane-1,2'-imidazo[1,2-a]pyrimidin]-5'-one

HRID 2408343Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[C:4]2[NH:11][C:10]3([CH2:15][CH2:14][CH2:13][CH2:12]3)[CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1C=CC(S(O[CH2:33][CH2:34][O:35][CH:36]([CH3:38])[CH3:37])(=O)=O)=CC=1.O>CC#N.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]2[N:11]([CH2:33][CH2:34][O:35][CH:36]([CH3:38])[CH3:37])[C:10]3([CH2:15][CH2:14][CH2:13][CH2:12]3)[CH2:9][N:5]2[C:6](=[O:8])[CH:7]=1

Participants

Conditions

Temperature: 65 °C

Procedure

0.200 g of 7′-chlorospiro[cyclopentane-1,2′-imidazo[1,2-a]pyrimidin]-5′-one are suspended in 7 mL of CH3CN, 0.70 g of cesium carbonate and 0.55 g of 2-isopropoxyethyl 4-methylbenzenesulfonate are added. The mixture is heated to 65° C. for 36 h. Water, ethyl acetate are added and then after decantation, the organic phase is dried with magnesium sulfate and then evaporated. The crude is purified by flash chromatography on silica gel (CH2Cl2/MeOH, 99/1). 0.17 g (yield=47%) of 7′-chloro-1′-(2-isopropoxyethyl)-spiro[cyclopentane-1,2′-imidazo[1,2-a]pyrimidin]-5′-one are obtained as a brown powder and including the following characteristics:

Workup

dry with materialafter decantation, the organic phase is dried with magnesium sulfate
customevaporated
customThe crude is purified by flash chromatography on silica gel (CH2Cl2/MeOH, 99/1)

Sources & evidence

ORD record: ord-cc8c1fc6f773474f8c6304a34e2b8d0d
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815853B2

Reaction notes

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