Ammonium fluoride → 5-Amino-3-[(2R,3R,5S)-3-(1-fluoro-1-methyl-ethyl)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione

HRID 60769

반응식

HRID 60769 반응식
[NH2:1][C:2]1[NH:3][C:4](=[O:40])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@H:12]3[C@H:16]([C:17]([F:20])([CH3:19])[CH3:18])[CH2:15][C@@H:14]([CH2:21][O:22][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)[O:13]3)[C:6]=2[N:7]=1.[NH4+].[F-]>CO>[NH2:1][C:2]1[NH:3][C:4](=[O:40])[C:5]2[S:10][C:9](=[O:11])[N:8]([C@H:12]3[C@H:16]([C:17]([F:20])([CH3:19])[CH3:18])[CH2:15][C@@H:14]([CH2:21][OH:22])[O:13]3)[C:6]=2[N:7]=1

참가 물질

4

반응물 2

HCID 25516Ammonium fluorideHCID 1371902235-amino-3-[(2R,3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(1-fluoro-1-methyl-ethyl)tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione2회

생성물 1

HCID 1371086975-Amino-3-[(2R,3R,5S)-3-(1-fluoro-1-methyl-ethyl)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione수율 24.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A mixture of 5-amino-3-[(2R,3R,5S)-5-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-(1-fluoro-1-methyl-ethyl)tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione (compound 40h, 66 mg, 0.12 mmol) and NH4F (133 mg, 3.6 mmol) in methanol was heated under reflux for 1.5 hrs. The resulting mixture was concentrated in vacuo and the residue was purified by preparative HPLC to afford 10 mg of 5-amino-3-[(2R,3R,5S)-3-(1-fluoro-1-methyl-ethyl)-5-(hydroxymethyl)tetrahydrofuran-2-yl]-6H-thiazolo[4,5-d]pyrimidine-2,7-dione (Example 40) as a white solid.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hrs
  3. concentrationThe resulting mixture was concentrated in vacuo
  4. customthe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-a4d00bd2e89e427383ca0c2294c38e0b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09441008B2

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