Potassium Carbonate → 5-amino-3-[(2R,3R,5S)-5-(1-hydroxypropyl)-3-prop-2-enyloxolan-2-yl]-6H-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione

HRID 60735노트

반응식

HRID 60735 반응식
C([O:9][CH:10]([C@@H:13]1[CH2:17][C@@H:16]([CH2:18][CH:19]=[CH2:20])[C@H:15]([N:21]2[C:25]3[N:26]=[C:27]([NH2:31])[NH:28][C:29](=[O:30])[C:24]=3[S:23][C:22]2=[O:32])[O:14]1)[CH2:11][CH3:12])(=O)C1C=CC=CC=1.C([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-]>CO>[CH2:18]([C@@H:16]1[CH2:17][C@@H:13]([CH:10]([OH:9])[CH2:11][CH3:12])[O:14][C@H:15]1[N:21]1[C:25]2[N:26]=[C:27]([NH2:31])[NH:28][C:29](=[O:30])[C:24]=2[S:23][C:22]1=[O:32])[CH:19]=[CH2:20]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 1371087171-[(2S,4R,5R)-4-allyl-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-2-yl]propyl benzoate2회

생성물 1

HCID 1371087595-amino-3-[(2R,3R,5S)-5-(1-hydroxypropyl)-3-prop-2-enyloxolan-2-yl]-6H-[1,3]thiazolo[4,5-d]pyrimidine-2,7-dione수율 32.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 1-[(2S,4R,5R)-4-allyl-5-(5-amino-2,7-dioxo-6H-thiazolo[4,5-d]pyrimidin-3-yl)tetrahydrofuran-2-yl]propyl benzoate (compound 26f, 800 mg, 1.75 mmol) in methanol (25 mL) was added K2CO3 (483 mg, 3.5 mmol). After being stirred at room temperature for 12 hours, the reaction was diluted by saturated NH4Cl solution and extracted with DCM. The organic layers were combined and concentrated in vacuo. The residue was purified by preparative HPLC to afford 200 mg of 3-[(2R,3R,5S)-3-allyl-5-(1-hydroxypropyl)tetrahydrofuran-2-yl]-5-amino-6H-thiazolo[4,5-d]pyrimidine-2,7-dione (Example 26). 100 mg of Example 26 was further separated by supercritical fluid chromatography (SFC) to afford 32.0 mg of Example 26-A and 30.8 mg of Example 26-B as white solid.

후처리

  1. extractionextracted with DCM
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-fbbab511873f42c28a60ff46bb78a2a8
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09441008B2

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