Hydrochloric Acid → HCID 19013275, compound

HRID 1729023Notes

Reaction equation

HRID 1729023 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][NH:19][C:20]2[N:25]=[C:24]([C:26](N)=[O:27])[CH:23]=[CH:22][N:21]=2)[CH2:13][CH2:12]1.[CH3:29][OH:30].Cl>C1CCCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[N:11]1[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][NH:19][C:20]2[N:25]=[C:24]([C:26]([O:30][CH3:29])=[O:27])[CH:23]=[CH:22][N:21]=2)[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 19013279HCID 19013279, compound

Product 1

HCID 19013275HCID 19013275, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

8.76 g (22.66 mmol) of 2-[[2-[4-(2,5-dimethoxyphenyl) piperazin-1-yl]ethyl]amino]pyrimidine-4-carboxamide are introduced into 650 ml of methanol in a 1 l round-bottomed flask, a stream of gaseous hydrochloric acid is passed through for a few minutes and the mixture is then heated at the reflux temperature of the methanol for 5 h. The solventis evaporated under reduced pressure, 300 ml of dichloromethane are added to the residue and the mixture is then basified with a saturated aqueous sodium hydrogencarbonate solution. The organic phase is dried over sodium sulphate, filtered and the solvent is then evaporated under reduced pressure. After purification by chromatography on a silica gel column (eluent: 100/0 to 90/10 dichloromethane/methanol mixture) and then by recrystallisation from cyclohexane, 6.93 g (17.26 mmol) of ester are isolated.

Workup

  1. customis passed through for a few minutes
  2. customThe solventis evaporated under reduced pressure, 300 ml of dichloromethane
  3. additionare added to the residue
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. filtrationfiltered
  6. customthe solvent is then evaporated under reduced pressure
  7. customAfter purification by chromatography on a silica gel column (eluent: 100/0 to 90/10 dichloromethane/methanol mixture)
  8. customare isolated

Sources & evidence

ORD record
ord-b678ec4ed35649babc7ee6263316ec03
Source dataset
uspto-grants-1994_07
Patent number
US05330985

Reaction notes

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