Cesium carbonate → (S)-1-[2-(4-benzyloxyphenyl)ethyl]-7-chloro-2-methyl-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one

HRID 633757Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 40 mL of DMF, 2 g (7.89 mmol) of (S)-7-chloro-2-methyl-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one, 3.44 g (11.84 mmol) of 1-benzyloxy-4-(2-bromoethyl)benzene and 5.14 g (15.78 mmol) of cesium carbonate is heated in a Biotage microwave reactor at 120° C. for 20 minutes. The reaction medium is evaporated to dryness. After purification by chromatography on silica gel (eluent A/B: heptane/EtOAc, gradient A/B: t 0 min 20% B, t 25 min 50% B, t 35 min 50% B), 2.8 g of (S)-1-[2-(4-benzyloxyphenyl)ethyl]-7-chloro-2-methyl-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one were obtained, corresponding to the following characteristics:

Workup

customThe reaction medium is evaporated to dryness
customAfter purification by chromatography on silica gel (eluent A/B: heptane/EtOAc, gradient A/B: t 0 min 20% B, t 25 min 50% B, t 35 min 50% B), 2.8 g of (S)-1-[2-(4-benzyloxyphenyl)ethyl]-7-chloro-2-methyl-2-trifluoromethyl-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one
customwere obtained, corresponding to the following characteristics

Sources & evidence

ORD record: ord-449f6419c64847728db625daf4599b37
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321790B2

Reaction notes

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