Hydrochloric Acid → 6-[(4-Amino-2-ethyl-5-pyrimidinyl)methyl]-7-methylthieno[2,3-c]pyridinium chloride hydrochloride

HRID 435776Notes

Reaction equation

HRID 435776 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([NH2:9])[C:6]([CH2:10]OC)=[CH:5][N:4]=1)[CH3:2].[CH3:13][C:14]1[N:15]=[CH:16][CH:17]=[C:18]2[CH:22]=[CH:21][S:20][C:19]=12.[ClH:23].N1C=CC=NC=1>C1(C)C(C)=CC=CC=1>[ClH:23].[Cl-:23].[NH2:9][C:7]1[C:6]([CH2:10][N+:15]2[C:14]([CH3:13])=[C:19]3[S:20][CH:21]=[CH:22][C:18]3=[CH:17][CH:16]=2)=[CH:5][N:4]=[C:3]([CH2:1][CH3:2])[N:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 9260PyrimidineHCID 2789027-Methylthieno[2,3-c]pyridineHCID 30165002-Ethyl-5-(methoxymethyl)-4-pyrimidinamine

Product 1

HCID 214166676-[(4-Amino-2-ethyl-5-pyrimidinyl)methyl]-7-methylthieno[2,3-c]pyridinium chloride hydrochloride

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
65 °C

Procedure

50 G. of 2-ethyl-4-amino-5-methoxymethyl pyrimidine, 50 g. of 7-methylthieno[2,3-c]pyridine and 500 ml. of xylene are placed in a 2-liter flask equipped with reflux condenser, stirrer, thermometer and gas inlet tube. Hydrogen chloride gas is added to this mixture over 30 minutes at a rate sufficient to add an amount equivalent to 0.2 moles, that of the pyrimidine. The temperature rises to about 67° C. The gas inlet tube is replaced with a distillation unit and the mixture heated at reflux (138° C.) for two hours during which fresh xylene is added to replace the volume of liquid that distills. An additional 25 g. of 7-methylthieno[2,3-c]pyridine are added and the mixture refluxed for 40 minutes. At the end of the reflux period, the reaction mixture is cooled to 65° C., the xylene decanted, and 50 ml. of acetonitrile added to the residue. The resulting mixture is stirred at room temperature for about 12 hours, filtered, and the solid 6-[(4-amino-2-ethyl-5-pyrimidinyl)methyl]-7-methylthieno-[2,3-c]pyridinium chloride hydrochloride thus obtained washed. The product has a m.p. of 249°-250° C., dec.

Workup

  1. customequipped
  2. temperaturewith reflux condenser, stirrer
  3. additionto add an amount equivalent to 0.2 moles
  4. customrises to about 67° C
  5. temperaturethe mixture heated
  6. additionis added
  7. distillationthat distills
  8. additionof 7-methylthieno[2,3-c]pyridine are added
  9. temperaturethe mixture refluxed for 40 minutes
  10. customthe xylene decanted
  11. additionof acetonitrile added to the residue
  12. filtrationfiltered

Sources & evidence

ORD record
ord-2d532f90de0d4d0ea262e7377df6c228
Source dataset
uspto-grants-1977_02
Patent number
US04006143

Reaction notes

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