Cyclopentylamine → Ethyl 4-(cyclopentylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylate

HRID 2386666Notes

Reaction equation

HRID 2386666 reaction equation
[CH:1]1([NH2:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:7]([O:9][C:10]([C:12]1[C:13](Cl)=[N:14][C:15]([S:18][CH3:19])=[N:16][CH:17]=1)=[O:11])[CH3:8]>C(Cl)Cl>[CH2:7]([O:9][C:10]([C:12]1[C:17]([NH:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:16][C:15]([S:18][CH3:19])=[N:14][CH:13]=1)=[O:11])[CH3:8]

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 9151473Ethyl 4-(cyclopentylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylateYield 105.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclopentylamine (12.7 mL, 129.3 mmol) was added to solution of 4-chloro-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester (10 g, 43.10 mmol) in DCM (250 mL) at RT and the resulting mixture was stirred for 3 days. The reaction mixture was washed 3 times with water; the aqueous extracts were combined and extracted twice with DCM. The combined organic extracts were dried over Na2SO4, filtered, and evaporated under reduced pressure to give 12.8 g of 4-cyclopentylamino-2-methylsulfanyl-pyrimidine-5-carboxylic acid ethyl ester as a crude oil without further purifications.

Workup

  1. washThe reaction mixture was washed 3 times with water
  2. extractionextracted twice with DCM
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0b0d845887234f148885e46885c6281d
Source dataset
uspto-grants-2012_09
Patent number
US08268840B2

Reaction notes

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