Water → HCID 59447008, compound

HRID 1746644Notes

Reaction equation

HRID 1746644 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[N:3]=1.[CH:13]1([CH2:19][NH2:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.C(N(CC)CC)C.O>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:5]=[C:6]([NH:20][CH2:19][CH:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[N:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 76688CyclohexanemethylamineHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylate

Product 1

HCID 59447008HCID 59447008, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A cooled (0° C.) solution of methyl 2,4-dichloropyrimidine-6-carboxylate (Apollo, OR2558, 2.62 g; 12.7 mmol) in anhydrous THF (95 mL) was treated with a solution of cyclohexanemethylamine (Aldrich, 1.68 mL; 12.66 mmol) and triethylamine (1.93 mL; 13.92 mmol) in THF (35 mL). The reaction mixture was stirred during 30 min. Water (50 mL) was poured into the reaction mixture, which was extracted with EtOAc. The combined organic extracts were dried over magnesium sulfate, filtered and concentrated, which was purified by column chromatography (silica) eluting with cyclohexane containing increasing amounts of EtOAc. The title product was obtained as a white solid.

Workup

  1. extractionwas extracted with EtOAc
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customwhich was purified by column chromatography (silica)
  6. washeluting with cyclohexane containing
  7. temperatureincreasing amounts of EtOAc

Sources & evidence

ORD record
ord-0bdd00bfb75949eb8dfbf01c51f9b937
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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