Diethyl Ether → 2,5-Methano-5H,9H-pyrimido(2,1-b)(1,5,3)dioxazepin-9-one, 2,3-dihydro-3-(hydroxymethyl)-8-methyl-, (2R,3R,5R)-

HRID 2072852

反応式

HRID 2072852 の反応式
[CH3:1][C:2]1[C:8](=[O:9])[NH:7][C:5](=O)[N:4]([C@@H:10]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:12]([OH:17])[C@H:11]2O)[CH:3]=1.C(=O)(OC1C=CC=CC=1)OC1C=CC=CC=1.C(OCC)C>CN(C=O)C.CO.C(=O)(O)[O-].[Na+]>[CH3:1][C:2]1[C:8](=[O:9])[N:7]=[C:5]2[N:4]([C@@H:10]3[O:14][C@H:13]([CH2:15][OH:16])[C@H:12]([O:17]2)[CH2:11]3)[CH:3]=1

参加物

7

反応物 3

HCID 3283Diethyl EtherHCID 7597Diphenyl carbonateHCID 4454085-Methyluridine

生成物 1

HCID 4579822,5-Methano-5H,9H-pyrimido(2,1-b)(1,5,3)dioxazepin-9-one, 2,3-dihydro-3-(hydroxymethyl)-8-methyl-, (2R,3R,5R)-収率 101.4%

試薬・触媒・溶媒 3

HCID 516892Sodium Bicarbonate触媒HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

A 100 mL round bottom flask equipped with magnetic stir bar, reflux condensor, and nitrogen inlet was charged with 5 g of ribothymidine, 4.7 g (1.2 eq) of diphenyl carbonate and 150 mg of sodium bicarbonate in 10 mL of DMF. The mixture was heated to 150° C. for 35 minutes. The black solution was diluted with 10 mL of MeOH and slowly added to 200 mL of diethyl ether. The tan product was filtered and dried to yield 4.4 g (96%) of anhydrothymidine.

後処理

  1. customA 100 mL round bottom flask equipped with magnetic stir bar
  2. temperaturereflux condensor, and nitrogen inlet
  3. filtrationThe tan product was filtered
  4. customdried

出典と根拠

ORDレコード
ord-c0b3691bde8f4128a9160c5ebc5206ac
出典データセット
uspto-grants-1990_04
特許番号
US04914233

関連ノート

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