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 1793810노트

반응식

HRID 1793810 반응식
[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

참가 물질

4

반응물 2

HCID 14817Phosphorus sulfide (P2S5)HCID 11994283HCID 11994283, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d5b1b8ca8d134a6cb03cd3a536fe322e
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022686B2

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