Triethylamine → (R)-2-methylsulfanyl-4-(tetrahydrofuran-3-ylamino)-pyrimidine-5-carboxylic acid ethyl ester

HRID 1243173노트

반응식

HRID 1243173 반응식
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.C(N(CC)CC)C.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:33][C@@H:34]1[CH2:38][CH2:37][O:36][CH2:35]1>O1CCOCC1>[CH2:11]([O:10][C:8]([C:7]1[C:2]([NH:33][C@@H:34]2[CH2:38][CH2:37][O:36][CH2:35]2)=[N:3][C:4]([S:13][CH3:14])=[N:5][CH:6]=1)=[O:9])[CH3:12]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl esterHCID 142431694-Methylbenzene-1-sulfonic acid--(3R)-oxolan-3-amine (1/1)

생성물 1

HCID 11150267(R)-2-methylsulfanyl-4-(tetrahydrofuran-3-ylamino)-pyrimidine-5-carboxylic acid ethyl ester

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A solution of ethyl 4-chloro-2-methylthio-5-pyrimidinecarboxylate (897 mg, 3.86 mmol) (Aldrich) and triethylamine (1.2 mL, 870 mg, 8.49 mmol) (Aldrich) in dioxane (20 mL) was treated with (R)-3-aminotetrahydrofuran p-toluene-sulfonic acid salt (1.0 g, 3.86 mmol) (Fluka). The mixture was stirred at reflux for 1 hour, then cooled and partitioned between brine and ethyl acetate. The organic layer was dried over sodium sulfate, filtered, concentrated and the residue was purified by chromatography with a silica gel column using a 0–100% ethyl acetate in hexanes gradient to give (R)-2-methylsulfanyl-4-(tetrahydrofuran-3-ylamino)-pyrimidine-5-carboxylic acid ethyl ester as a colorless viscous oil. (Yield 1.0 g, 92%).

후처리

  1. temperatureat reflux for 1 hour
  2. temperaturecooled
  3. custompartitioned between brine and ethyl acetate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe residue was purified by chromatography with a silica gel column

출처 및 근거

ORD 기록
ord-cb68d6f41f2d4a38bcfa649137dc64df
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115740B2

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