3-Methyl-2-methoxycarbonylcyclopentanone → HCID 178423154, compound

HRID 1010867Notes

Reaction equation

HRID 1010867 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:3]=1[C:4]([NH2:6])=[NH:5].C([O:14][C:15]([CH:17]1[C:21](=O)[CH2:20][CH2:19][CH:18]1[CH3:23])=O)C>CCO>[Cl:11][C:8]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([C:4]2[N:6]=[C:15]([OH:14])[C:17]3[CH:18]([CH3:23])[CH2:19][CH2:20][C:21]=3[N:5]=2)[CH:7]=1

Participants

4

Reactant 2

HCID 5601313-Methyl-2-methoxycarbonylcyclopentanoneHCID 219309795-Chloro-2-fluorobenzene-1-carboximidamide

Product 1

HCID 178423154HCID 178423154, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

To a solution of 2-fluoro-5-chlorobenzamidine (1.95 g, 11.27 mmol, 1.1 eq) in EtOH (20 ml) was added a solution of 2-methyl-5-oxo cyclopentanecarboxylic acid ethyl ester (prepared according to Wang, C.; Gu, X.; Yu, M. S.; Curran, D. P.: Tetrahedron, 1998, 29, 8355-8370; 1.60 g, 10.26 mmol, 1 eq) in ethanol (5 ml). The reaction mixture was heated to 80° C. overnight. The reaction mixture was cooled to r.t. and the solvent was removed in vacuo to give a crude residue which was purified by recrystallization from hot ethyl acetate to give 2-(5-chloro-2-fluorophenyl)-5-methyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ol (1.0 g, 35%) as a white crystalline solid and the filtrate was further purified by flash column chromatography to give another 850 mg of 2-(5-chloro-2-fluorophenyl)-5-methyl-6,7-dihydro-5H-cyclopentapyrimidin-4-ol.

Workup

  1. temperatureThe reaction mixture was cooled to r.t.
  2. customthe solvent was removed in vacuo
  3. customto give a crude residue which
  4. customwas purified by recrystallization from hot ethyl acetate

Sources & evidence

ORD record
ord-49ad16cc430648da927861cb62ea40f2
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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