Triethylamine → Methyl 2-chloro-6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylate

HRID 1946667노트

반응식

HRID 1946667 반응식
[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.C(N(CC)CC)C.Cl.[CH:21]1([NH:27][CH2:28][CH:29]2[CH2:31][CH2:30]2)[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>C1COCC1>[Cl:1][C:2]1[N:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:5]=[C:6]([N:27]([CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]2)[CH2:28][CH:29]2[CH2:31][CH2:30]2)[N:7]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylateHCID 16641250N-(Cyclopropylmethyl)cyclohexanamine hydrochloride

생성물 1

HCID 59446993Methyl 2-chloro-6-[cyclohexyl(cyclopropylmethyl)amino]pyrimidine-4-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A cooled (0° C.) solution of methyl 2,4-dichloropyrimidine-6-carboxylate (Apollo, OR2558, 5.00 g; 24.1 mmol) in THF (50 mL) was treated triethylamine (7.38 ml; 53.1 mmol) and cyclohexyl(cyclopropylmethyl)amine hydrochloride (Chembridge, 4.58 g; 24.1 mmol. The reaction mixture was stirred for 2 days at RT. The solvent was evaporated under reduced pressure, the remaining residue was partitioned between 100 ml of ethyl acetate and a saturated aqueous solution of NH4Cl (50 mL). The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated to obtain the crude product, which was purified by column chromatography (silica) eluting with cyclohexane containing increasing amounts of EtOAc to give the title product as a yellow oil, which solidified upon standing (6.14 g, 78%).

후처리

  1. customThe solvent was evaporated under reduced pressure
  2. customthe remaining residue was partitioned between 100 ml of ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto obtain the crude product, which
  8. customwas purified by column chromatography (silica)
  9. washeluting with cyclohexane containing
  10. temperatureincreasing amounts of EtOAc

출처 및 근거

ORD 기록
ord-33eda11970ee4e9a99c0dbea1159cd53
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399448B2

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