(2Rs,5rs)-4-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-n-butyramidine → (2Rs,5rs)-2-{3-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propyl}-4,6-dimethyl-pyrimidine

HRID 890303Notes

Reaction equation

HRID 890303 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:15])=[O:14])[CH:11]([CH2:23][CH2:24][CH2:25][C:26]([NH2:28])=[NH:27])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1>CC(=O)CC(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([S:13]([C:16]3[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=3)(=[O:14])=[O:15])[CH:11]([CH2:23][CH2:24][CH2:25][C:26]3[N:28]=[C:7]([CH3:6])[CH:2]=[C:3]([CH3:4])[N:27]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 22250424(2Rs,5rs)-4-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-n-butyramidine

Product 1

HCID 22250488(2Rs,5rs)-2-{3-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propyl}-4,6-dimethyl-pyrimidineYield 73.7%

Reagents, catalysts & solvents 1

HCID 31261AcetylacetoneSolvent

Procedure

A stirred solution of (2RS,5RS)-4-[5-(4-fluoro-phenyl)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-N-butyramidine (0.35 g, 0.87 mmol) in pentan-2,4-dione (7 ml) was heated for 3 h at 125° C. Evaporation and purification by column chromatography on silica gel (ethyl acetate) yielded the title compound (0.15 g, 38%) as a light yellow oil, MS: m/e=468.3 (M+H+).

Workup

  1. customEvaporation and purification by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-6dfe6961eb5f473d9464aed4d0a4fba3
Source dataset
uspto-grants-2006_02
Patent number
US06995182B2

Reaction notes

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