Hydrochloric Acid → 5-Amino-2-{2-[(5-dimethylaminomethyl-3-thienyl)methylthio]ethylamino}-4(3H)-pyrimidone

HRID 622785Notes

Reaction equation

HRID 622785 reaction equation
[N+:1]([C:4]1[C:5](=[O:24])[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]([CH3:23])[CH3:22])[S:17][CH:16]=2)=[N:8][CH:9]=1)([O-])=O.Cl>[Ni].CO>[NH2:1][C:4]1[C:5](=[O:24])[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]([CH3:22])[CH3:23])[S:17][CH:16]=2)=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 143266985-Nitro-2-{2-[(5-dimethylaminomethyl-3-thienyl)methylthio]ethylamino}-4(3H)-pyrimidone

Product 1

HCID 212920325-Amino-2-{2-[(5-dimethylaminomethyl-3-thienyl)methylthio]ethylamino}-4(3H)-pyrimidoneYield 34.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-nitro-2-{2-[(5-dimethylaminomethyl-3-thienyl)methylthio]ethylamino}-4(3H)-pyrimidone (1.3 g; 3.51 mmoles) and a catalytic amount of Raney nickel No. 28 (approximately 1.4 cm3) in 108 ml of methanol was hydrogenated in a Parr apparatus at 50 psi for 2.5 hours. The reaction mixture was filtered, treated with 1.55N methanolic hydrochloric acid (7.0 ml, 10.9 meq.) and then evaporated under reduced pressure. The residue was placed on 85 g of silica gel and chromatographed by flash chromatography using a gradient elution of methanol:CH2Cl2 :H2O from 20:80:1 to 30:70:1. The appropriate fractions were combined and treated with 7.0 ml of 1.55N methanolic HCl, and then evaporated under reduced pressure and dried under high vacuum at 56° C. for 6 hours to give 0.41 g of the title compound as a trihydrochloride salt which had an indeterminate melting point. The NMR spectrum (100 MHz) in d6 dimethyl sulfoxide gave the following resonances δ: 8.88 (m, 6H); 8.18 (m, 1H), 7.82 (s, 1H), 7.56 (s, 1H), 7.40 (s, 1H); 4.50 (s, 2H); 3.82 (s, 2H); 3.50 (m, 2H); 2.73 (m, 8H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customevaporated under reduced pressure
  3. customchromatographed by flash chromatography
  4. washa gradient elution of methanol
  5. additiontreated with 7.0 ml of 1.55N methanolic HCl
  6. customevaporated under reduced pressure
  7. customdried under high vacuum at 56° C. for 6 hours

Sources & evidence

ORD record
ord-d7ed171691e04ad0b442e91351b27f60
Source dataset
uspto-grants-1988_09
Patent number
US04772704

Reaction notes

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