Phosphoric Acid → HCID 21998636、化合物

HRID 1976557ノート

反応式

HRID 1976557 の反応式
[NH2:1][C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:10]=2)[C:6](=[S:25])[NH:5][C:4](=[O:26])[CH:3]=1.P(=O)(O)(O)O.[N:32]([O-])=O.[Na+].S(S([O-])=O)([O-])=O.[Na+].[Na+]>CS(C)=O.C1COCC1.O.CO>[CH2:18]([O:17][C:11]1[CH:10]=[C:9]([CH:14]=[CH:13][C:12]=1[O:15][CH3:16])[CH2:8][N:7]1[C:2]([NH2:1])=[C:3]([NH2:32])[C:4](=[O:26])[NH:5][C:6]1=[S:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

9

反応物 4

HCID 1004Phosphoric AcidHCID 24489Sodium DithioniteHCID 21998640HCID 21998640、化合物HCID 23668193Sodium Nitrite

生成物 1

HCID 21998636HCID 21998636、化合物収率 105.6%

試薬・触媒・溶媒 4

HCID 679Dimethyl Sulfoxide溶媒HCID 887Methanol溶媒HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
30 °C

実験手順

6-amino-1-(3-benzyloxy-4-methoxy-benzyl)-2-thiouracil (36.94 g, 100 mmole) was dissolved in DMSO (74 ml), diluted with THF (185 ml) and treated with 85% phosphoric acid (7.46 ml). At 55-60° C., 4M sodium nitrite (30 ml, 120 mmole) was added slowly. After 30 minutes, methanol (10 ml) was added, the reaction was cooled to 30° C., and a suspension of 85% sodium dithionite (40.96 g, 200 mmole) in water (80 ml) was added slowly. After the addition of water (200 ml) the solvent was removed in vacuo and the suspension diluted with water to 1 l. The solid was collected at 0-5° C. to give crude 1-(3-benzyloxy-4-methoxy-benzyl)-5,6-diamino-2-thiouracil (40.58 g).

後処理

  1. additionwas added slowly
  2. customwas removed in vacuo
  3. additionthe suspension diluted with water to 1 l
  4. customThe solid was collected at 0-5° C.

出典と根拠

ORDレコード
ord-05dd7cdb56884f718e51d83ff574f2ff
出典データセット
uspto-grants-2001_05
特許番号
US06228859B1

反応ノート

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