Sodium Cyanide → 4-[(2,3,4,6-Tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxo-1H-pyrrolo[3,4-d]pyrimidin-5-yl)thio]butanenitrile

HRID 381302노트

반응식

HRID 381302 반응식
CS(O[CH2:6][CH2:7][CH2:8][S:9][C:10]1[N:11]([CH2:26][C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)[CH:12]=[C:13]2[C:18]=1[C:17](=[O:19])[N:16]([CH3:20])[C:15](=[O:21])[N:14]2[CH2:22][CH:23]([CH3:25])[CH3:24])(=O)=O.[C-:37]#[N:38].[Na+]>CN(C)C=O>[CH3:20][N:16]1[C:17](=[O:19])[C:18]2=[C:10]([S:9][CH2:8][CH2:7][CH2:6][C:37]#[N:38])[N:11]([CH2:26][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:30]=[CH:29][CH:28]=3)[CH:12]=[C:13]2[N:14]([CH2:22][CH:23]([CH3:24])[CH3:25])[C:15]1=[O:21]

참가 물질

4

반응물 2

HCID 8929Sodium CyanideHCID 183629375-[(3-{Methanesulphonyloxy}propyl)thio]-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione

생성물 1

HCID 183629264-[(2,3,4,6-Tetrahydro-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-2,4-dioxo-1H-pyrrolo[3,4-d]pyrimidin-5-yl)thio]butanenitrile수율 27.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5-[(3-{Methanesulphonyloxy}propyl)thio]-3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-dione (391 mg) was dissolved in dimethyformamide (15 ml) and sodium cyanide (254 mg) was added. The mixture was sonicated for 4 hours and then poured onto sodium bicarbonate (aqueous). The mixture was extracted thrice with ethyl acetate, the extracts were combined, washed twice with water and once with brine, then dried, filtered and evaporated. The resultant oil was chromatographed, eluting with ethyl acetate : isohexane (4:5) and then triturated with cyclohexane-ethyl acetate to give the title compound (95 mg).

후처리

  1. customThe mixture was sonicated for 4 hours
  2. additionpoured onto sodium bicarbonate (aqueous)
  3. extractionThe mixture was extracted thrice with ethyl acetate
  4. washwashed twice with water and once with brine
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe resultant oil was chromatographed
  9. washeluting with ethyl acetate : isohexane (4:5)
  10. customtriturated with cyclohexane-ethyl acetate

출처 및 근거

ORD 기록
ord-0066269cdc6d4045b262ffad8ad2acdb
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06306863B1

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