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

反応式

HRID 60769 の反応式
[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

参加物

4

反応物 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-dione2 回

生成物 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-dione収率 24.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a4d00bd2e89e427383ca0c2294c38e0b
出典データセット
uspto-grants-2016_09
特許番号
US09441008B2

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