Ethanol → 2-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(3-pyridyl)methyl-4-pyrimidone

HRID 358460Notes

Reaction equation

HRID 358460 reaction equation
[N+]([NH:4][C:5]1[NH:10][C:9](=[O:11])[C:8]([CH2:12][C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:7][N:6]=1)([O-])=O.[CH3:19][N:20]([CH2:22][C:23]1[S:24][CH:25]=[C:26]([CH2:28][S:29][CH2:30][CH2:31]N)[N:27]=1)[CH3:21].C(O)C>O>[CH3:21][N:20]([CH2:22][C:23]1[S:24][CH:25]=[C:26]([CH2:28][S:29][CH2:30][CH2:31][NH:4][C:5]2[NH:10][C:9](=[O:11])[C:8]([CH2:12][C:13]3[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=3)=[CH:7][N:6]=2)[N:27]=1)[CH3:19]

Participants

5

Reactant 3

HCID 702EthanolHCID 109773182-(Dimethylaminomethyl)-4-(2-aminoethylthiomethyl)thiazoleHCID 12788688N-{6-Oxo-5-[(pyridin-3-yl)methyl]-1,6-dihydropyrimidin-2-yl}nitramide

Product 1

HCID 133734772-[2-(2-Dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(3-pyridyl)methyl-4-pyrimidone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A reaction mixture prepared from 1.24 g. of 2-nitroamino-5-(3-pyridyl)methyl-4-pyrimidone, 1.14 g. of 2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethylamine and 6 ml. of anhydrous ethanol was refluxed for about 1 day under a nitrogen atmosphere. The volatile constitutents were removed by evaporation to yield an oily residue. Water was added and the aqueous layer extracted with ether and with ethyl acetate. The organic extracts were combined, dried and evaporated to dryness to yield 2-[2-(2-dimethylaminomethyl-4-thiazolylmethylthio)ethyl]amino-5-(3-pyridyl)methyl-4-pyrimidone as a residue which was crystallized from ether. Recrystallization from an ethanol-ether solvent mixture yielded 2-[2-(2-dimethylaminomethyle-4-thiazolylmethylthio)ethyl]amino-5-(3-pyridyl)methyl-4-pyrimidone melting at 122°-123° C.; yield=0.68 g.

Workup

  1. customA reaction mixture prepared from 1.24 g
  2. customThe volatile constitutents were removed by evaporation
  3. customto yield an oily residue
  4. extractionthe aqueous layer extracted with ether and with ethyl acetate
  5. customdried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-d2e4b20cefc24253b89817d5bff47df1
Source dataset
uspto-grants-1984_08
Patent number
US04468399

Reaction notes

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