4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → HCID 71237152, compound

HRID 2280717Notes

Reaction equation

HRID 2280717 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=1.FC(F)(F)C(O)=O.[CH3:22][O:23][C@H:24]1[CH2:29][CH2:28][CH2:27][C@@H:26]([NH2:30])[CH2:25]1.CCN(C(C)C)C(C)C>C(O)C>[CH3:22][O:23][C@H:24]1[CH2:29][CH2:28][CH2:27][C@@H:26]([NH:30][C:2]2[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([S:13][CH3:14])[N:3]=2)[CH2:25]1

Participants

5

Reactant 3

HCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 81531DiisopropylethylamineHCID 71237318HCID 71237318, compound

Product 1

HCID 71237152HCID 71237152, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirring solution of ethyl 4-chloro-2-(methylthio)-pyrimidine-5-carboxylate (1.084 g, 4.66 mmol) and (1R,3S)-3-methoxycyclohexanamine trifluoroacetate (1.133 g, 4.66 mmol) in ethanol (18.63 mL) was added DIEA (2.434 mL, 13.97 mmol). The reaction mixture was heated to 60° C. for 17 h. The reaction was removed from heat, cooled to room temperature and concentrated. The crude material was purified by silica gel chromatography (0-25% ethyl acetate in hexanes) to afford ethyl 4-((1R,3S)-3-methoxycyclohexylamino)-2-(methylthio)pyrimidine-5-carboxylate (1.4284 g, 4.39 mmol, 94% yield) as a clear oil. MS (ESI) m/z 326.2 [M+1]+.

Workup

  1. customThe reaction was removed
  2. temperaturefrom heat
  3. temperaturecooled to room temperature
  4. concentrationconcentrated
  5. customThe crude material was purified by silica gel chromatography (0-25% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c888e301dcff4bb0a779249f51c08bb2
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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