Water → HCID 75464918, compound

HRID 2112748Notes

Reaction equation

HRID 2112748 reaction equation
Cl.C([N:9]1[CH2:20][CH2:19][C:12]2[N:13]=[C:14]([Cl:18])[N:15]=[C:16]([Cl:17])[C:11]=2[CH2:10]1)C1C=CC=CC=1.C(N(CC)CC)C.Cl[C:29]([O:31][CH:32]([Cl:34])[CH3:33])=[O:30].O>ClCCCl>[Cl:18][C:14]1[N:15]=[C:16]([Cl:17])[C:11]2[CH2:10][N:9]([C:29]([O:31][CH:32]([Cl:34])[CH3:33])=[O:30])[CH2:20][CH2:19][C:12]=2[N:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 5213051-Chloroethyl chloroformateHCID 49759226HCID 49759226, compound

Product 1

HCID 75464918HCID 75464918, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

6-Benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride (35.0 g, 0.106 mol) prepared according to Process Step 2 was dissolved in 1,2-dichloroethane (850 mL), and the solution was mixed with triethylamine (14.9 mL, 0.107 mol) and 1-chloroethyl chloroformate (34.1 mL, 0.316 mol), followed by stirring under reflux for five hours. After checking the completion of the reaction by thin layer chromatography, the reaction mixture was cooled and was mixed with water, followed by separation. The organic layer was washed with brine, was dried over anhydrous magnesium sulfate and was concentrated. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1) and thereby yielded a 2,4-dichloro-6-(1-chloroethoxycarbonyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine fraction. After distilling off the solvent, the residue was dissolved in methanol (850 mL), followed by stirring under reflux for one hour. After checking the completion of the reaction by thin layer chromatography, the reaction mixture was concentrated and thereby yielded 2,4-dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride (23.5 g, in a total yield from 6-benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine hydrochloride of 95%).

Workup

  1. temperatureunder reflux for five hours
  2. customthe completion of the reaction by thin layer chromatography
  3. temperaturethe reaction mixture was cooled
  4. customfollowed by separation
  5. washThe organic layer was washed with brine
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. concentrationwas concentrated
  8. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-b24c9b1b11a34536b80df8f72aa52e01
Source dataset
uspto-grants-2009_04
Patent number
US07524852B2

Reaction notes

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