Hydrochloric Acid → HCID 14326701, compound

HRID 622786Notes

Reaction equation

HRID 622786 reaction equation
[N+:1]([C:4]1[C:5](=[O:27])[NH:6][C:7]([NH:10][CH2:11][CH2:12][S:13][CH2:14][C:15]2[CH:19]=[C:18]([CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)[S:17][CH:16]=2)=[N:8][CH:9]=1)([O-])=O.Cl>[Ni].CO>[NH2:1][C:4]1[C:5](=[O:27])[NH:6][C:7]([NH:10][CH2:11][CH2:12][S:13][CH2:14][C:15]2[CH:19]=[C:18]([CH2:20][N:21]3[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]3)[S:17][CH:16]=2)=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 14326699HCID 14326699, compound

Product 1

HCID 14326701HCID 14326701, compoundYield 47.8%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-nitro-2-{2-[(5-piperidinomethyl-3-thienyl)methylthio]ethylamino}-4(3H)-pyrimidone (5.32 g; 12.96 mmoles) and a catalytic amount of Raney nickel No. 28 (approximately 3.5 cm3) in 300 ml of methanol was hydrogenated in a Parr apparatus at 50 psi for 3.0 hours. The reaction mixture was filtered, treated with 1.55N methanolic HCl (24.0 ml; 37.2 meq.) and evaporated under reduced pressure. The residue was placed on 180 g of silica gel and chromatographed by flash chromatography using a gradient elution of methanol-methylene chloride. The appropriate fractions were combined, evaporated and then rechromatographed using a gradient elution of CH3CN:CH3OH:CH2Cl2 from 7:14:86 to 8:18:80. The appropriate fractions were combined and treated with 20 ml of 1.55N methanolic HCl, and then evaporated under reduced pressure and dried under high vacuum at 56° C. to give 2.35 g of the title compound as a trihydrochloride, mp 150°-155° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated under reduced pressure
  3. customchromatographed by flash chromatography
  4. washa gradient elution of methanol-methylene chloride
  5. customevaporated
  6. customrechromatographed
  7. washa gradient elution of CH3CN
  8. additiontreated with 20 ml of 1.55N methanolic HCl
  9. customevaporated under reduced pressure
  10. customdried under high vacuum at 56° C.

Sources & evidence

ORD record
ord-4095a7f0ad6940e8a4ff030e16700849
Source dataset
uspto-grants-1988_09
Patent number
US04772704

Reaction notes

Loading…