Water → (S)-Ethyl 2-chloro-4-(1-(5-fluoropyridin-2-yl)ethylamino)pyrimidine-5-carboxylate

HRID 573977Notes

Reaction equation

HRID 573977 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=1.Cl.[F:15][C:16]1[CH:17]=[CH:18][C:19]([C@@H:22]([NH2:24])[CH3:23])=[N:20][CH:21]=1.C(N(C(C)C)CC)(C)C.O>C(#N)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:24][C@H:22]([C:19]2[CH:18]=[CH:17][C:16]([F:15])=[CH:21][N:20]=2)[CH3:23])[C:5]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 104020Ethyl 2,4-dichloropyrimidine-5-carboxylateHCID 67123789(S)-1-(5-fluoropyridin-2-yl)ethanamine hydrochloride

Product 1

HCID 123343309(S)-Ethyl 2-chloro-4-(1-(5-fluoropyridin-2-yl)ethylamino)pyrimidine-5-carboxylateYield 115.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of ethyl 2,4-dichloropyrimidine-5-carboxylate (prepared as described in WO2009/131687, 0.29 g, 1.31 mmol), (S)-1-(5-fluoropyridin-2-yl)ethanamine hydrochloride (prepared as described in WO2006/123113, 0.28 g, 1.59 mmol) and diisopropylethylamine (0.69 mL, 3.96 mmol) in acetonitrile (3 mL) was stirred overnight at ambient temperature. Water was then added and the reaction mixture was extracted with diethyl ether. The organic phase was washed with water and brine, dried (MgSO4), filtered and the solvents evaporated under reduced pressure to yield the title compound (0.49 g, 85%) as an oil.

Workup

  1. extractionthe reaction mixture was extracted with diethyl ether
  2. washThe organic phase was washed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvents evaporated under reduced pressure

Sources & evidence

ORD record
ord-f003129489d548f5a4f2c7df81b6bbb5
Source dataset
uspto-grants-2015_05
Patent number
US09034311B2

Reaction notes

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