Cyclopentylamine → HCID 22325500, compound

HRID 987517Notes

Reaction equation

HRID 987517 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])=[C:6]([Cl:15])[N:5]=[C:4]([S:16][CH3:17])[N:3]=1.[CH:18]1([NH2:23])[CH2:22][CH2:21][CH2:20][CH2:19]1.C(OCC)(=O)C>C(Cl)Cl.C(OC(=O)C)C.C(OCC)C>[Cl:15][C:6]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[F:14])=[C:2]([NH:23][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[N:3]=[C:4]([S:16][CH3:17])[N:5]=1

Participants

6

Reactant 3

HCID 2906CyclopentylamineHCID 8857Ethyl AcetateHCID 22325501HCID 22325501, compound

Product 1

HCID 22325500HCID 22325500, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21584169Diethylether ethylacetateSolvent

Procedure

To a solution of 4,6-dichloro-5-(2-fluorophenyl)-2-methylthiopyrimidine (0.74 g, 256 mmol) in methylene chloride (1 ml) at room temperature under nitrogen atmosphere was added cyclopentyl-amine (1.01 ml, 10.24 mmol) and the reaction mixture was stirred at room temperature for 15 hours. The reaction mixture was then diluted with 1:1 v/v diethyl ether ethyl acetate (75 ml), washed with 1M aqueous hydrochloric acid (2×75 ml), saturated aqueous sodium bicarbonate solution (75 ml) and saturated brine (75 ml), dried over magnesium sulfate and concentrated in vacuo to afford a colorless syrup. The crude product was chromatographed on silica gel eluting with 95:5 v/v hexane: ethyl acetate to afford 0.87 g (100% yield) of the title compound as a white crystalline solid (melting point: 81-83° C.).

Workup

  1. washwashed with 1M aqueous hydrochloric acid (2×75 ml), saturated aqueous sodium bicarbonate solution (75 ml) and saturated brine (75 ml)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customto afford a colorless syrup
  5. customThe crude product was chromatographed on silica gel eluting with 95:5 v/v hexane

Sources & evidence

ORD record
ord-26c38fa0c9b84626a8a2f91ce957e5c5
Source dataset
uspto-grants-2003_10
Patent number
US06632821B2

Reaction notes

Loading…