4-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester → HCID 70981290, compound

HRID 2280700Notes

Reaction equation

HRID 2280700 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.[NH2:15][C@H:16]1[CH2:20][CH2:19][CH2:18][C@H:17]1[CH2:21][OH:22].CCN(C(C)C)C(C)C>C(O)C>[OH:22][CH2:21][C@H:17]1[CH2:18][CH2:19][CH2:20][C@H:16]1[NH:15][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

Participants

5

Reactant 3

HCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 81531DiisopropylethylamineHCID 13514420[(1R,2S)-2-Aminocyclopentyl]methanol

Product 1

HCID 70981290HCID 70981290, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

To a stirred solution of ethyl 4-chloro-2-(methylthio)-pyrimidine-5-carboxylate (5.00 g, 21.49 mmol) and cis-(2-aminocyclopentyl)-methanol (2.60 g, 22.56 mmol) in ethanol (85 mL) was added DIEA (5.61 mL, 32.2 mmol) and heated to 60° C. for 2.5 h. Upon completion of reaction, as indicated by LCMS and TLC, the reaction was removed from heat and concentrated, then purified by silica gel chromatography (0-80% ethyl acetate/hexane). The desired product fractions were combined and concentrated to afford ethyl 4-(cis-2-(hydroxymethyl)cyclopentylamino)-2-(methylthio)pyrimidine-5-carboxylate (6.4 g, 96% yield) as a white solid. MS (ESI) m/z 312.4 [M+1]+.

Workup

  1. customUpon completion of reaction
  2. customthe reaction was removed
  3. temperaturefrom heat
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (0-80% ethyl acetate/hexane)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-55045f540bff46bdb199b278e69a263b
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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