Phosphorus sulfide (P2S5) → 8-(4-Hydroxy-bicyclo[2.2.2]oct-1-yl)-3-propyl-6-thioxo-1,3,6,7-tetrahydro-purin-2-one

HRID 395275ノート

反応式

HRID 395275 の反応式
[OH:1][C:2]12[CH2:9][CH2:8][C:5]([C:10]3[NH:18][C:17]4[C:16](=O)[NH:15][C:14](=[O:20])[N:13]([CH2:21][CH2:22][CH3:23])[C:12]=4[N:11]=3)([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:25]>N1C=CC=CC=1>[OH:1][C:2]12[CH2:9][CH2:8][C:5]([C:10]3[NH:18][C:17]4[C:16](=[S:25])[NH:15][C:14](=[O:20])[N:13]([CH2:21][CH2:22][CH3:23])[C:12]=4[N:11]=3)([CH2:6][CH2:7]1)[CH2:4][CH2:3]2

参加物

4

反応物 2

HCID 14817Phosphorus sulfide (P2S5)HCID 11994283HCID 11994283、化合物

生成物 1

HCID 119956538-(4-Hydroxy-bicyclo[2.2.2]oct-1-yl)-3-propyl-6-thioxo-1,3,6,7-tetrahydro-purin-2-one収率 19%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

8-(4-Hydroxy-bicyclo[2.2.2]oct-1-yl)-3-propyl-3,7-dihydro-purine-2,6-dione (500 mg, 1.57 mmol) was dissolved in 10 mL of pyridine. P4S10 (1.05 g, 1.5 eq) was added and the reaction mixture was stirred under reflux for 6 h. The reaction mixture was then cooled to rt and quenched slowly with 5 mL of H2O. The mixture was then acidified at 0° C. to pH 5 with 6 N HCl. The aqueous layer was extracted with EtOAc. The combined organic layer was dried (Na2SO4) and concentrated under reduced pressure. Purification by preparative HPLC afforded 100 mg of the titled compound.

後処理

  1. temperatureunder reflux for 6 h
  2. customquenched slowly with 5 mL of H2O
  3. customwas then acidified at 0° C. to pH 5 with 6 N HCl
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organic layer was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by preparative HPLC

出典と根拠

ORDレコード
ord-c499d584c769481088eb1dba97848fcd
出典データセット
uspto-grants-2003_08
特許番号
US06605601B2

反応ノート

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