5-Bromouracil → HCID 66649606、化合物

HRID 419788

反応式

HRID 419788 の反応式
C(O[C@H:5]1[O:27][C@@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C@@H:6]1[O:7][C:8](=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=O)C.[Br:38][C:39]1[C:40](=[O:46])[NH:41][C:42](=[O:45])[NH:43][CH:44]=1.C[Si](N[Si](C)(C)C)(C)C.C[Si](Cl)(C)C>CC#N>[C:8]([O:7][C@H:6]1[C@@H:16]([O:17][C:18](=[O:25])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C@H:26]([CH2:28][O:29][C:30](=[O:37])[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[O:27][C@@H:5]1[N:43]1[CH:44]=[C:39]([Br:38])[C:40](=[O:46])[NH:41][C:42]1=[O:45])(=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

6

反応物 4

HCID 58025-BromouracilHCID 6397ChlorotrimethylsilaneHCID 13838HexamethyldisilazaneHCID 10973190Ribofuranose, 1-acetate 2,3,5-tribenzoate

生成物 1

HCID 66649606HCID 66649606、化合物収率 98.6%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

A solution of 1-O-acetyl-2,3,5-tri-O-benzoyl-β-L-ribofuranose (2.3 g, 4.55 mmol) in CH3CN (30 mL) was added to silylated 5-bromouracil [generated from 5-bromouracil (2.2 g, 14.3 mmol), HMDS (10 mL), and TMSCl (0.2 mL) by heating for 2 h at 80° C. followed by evaporation of the solvents], and the mixture cooled to 0° C. 1 M SnCl4 (13.6 mL) was added drop-wise, and the mixture stirred for 2 h at room temperature. The mixture was diluted with CHCl3 (100 mL) and quenched with cold saturated NaHCO3. The mixture was filtered over a Celite pad, and the organic phase separated, dried (MgSO4), and evaporated to give a white solid. The solid was washed with cold EtOAc and crystallized from EtOAc in hexanes to give the title compound (2.85 g, 98%) as a white crystals. 1H-NMR (CDCl3) δ 8.06 (1H, br s, NH), 8.06-7.29 (15H, m, Bz) 7.68 (1H, s, H-6), 6.29 (1H, d, H-1′, J=6 Hz), 5.81 (1H, m, H-3′), 5.65 (1H, t, H-2′, J=6 Hz), 4.77-4.62 (3H, m, H-4′, H-5′a, and 5′b).

後処理

  1. customfollowed by evaporation of the solvents], and the mixture
  2. temperaturecooled to 0° C
  3. addition1 M SnCl4 (13.6 mL) was added drop-wise
  4. additionThe mixture was diluted with CHCl3 (100 mL)
  5. customquenched with cold saturated NaHCO3
  6. filtrationThe mixture was filtered over a Celite pad
  7. customthe organic phase separated
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customto give a white solid
  11. washThe solid was washed with cold EtOAc
  12. customcrystallized from EtOAc in hexanes

出典と根拠

ORDレコード
ord-2cee8f88bb2f4c9fa49c06c489b2d4d3
出典データセット
uspto-grants-2012_01
特許番号
US08093380B2

関連ノート

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