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 381302Notes

Reaction equation

HRID 381302 reaction equation
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]

Participants

4

Reactant 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

Product 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]butanenitrileYield 27.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0066269cdc6d4045b262ffad8ad2acdb
Source dataset
uspto-grants-2001_10
Patent number
US06306863B1

Reaction notes

Loading…