N,N-Dimethylaniline → 7-Benzyl-4-chloro-2-(methylthio)-5,6,7,8-tetrahydropyrido[3,4-D]pyrimidine

HRID 971224Notes

Reaction equation

HRID 971224 reaction equation
CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:12])=O.[CH2:15]([N:22]1[CH2:31][CH2:30][CH:29]2[C:24](=[N:25][C:26]([S:33][CH3:34])=[N:27][C:28]2=O)[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl>[CH2:15]([N:22]1[CH2:31][CH2:30][C:29]2[C:28]([Cl:12])=[N:27][C:26]([S:33][CH3:34])=[N:25][C:24]=2[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 692223017-Benzyl-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4(4aH)-one

Product 1

HCID 529876597-Benzyl-4-chloro-2-(methylthio)-5,6,7,8-tetrahydropyrido[3,4-D]pyrimidine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

N,N-Dimethylaniline (3.2 g, 26.6 mmol) and phosphorus oxychloride (32.6 g, 213 mmol) were added to the solution of 7-benzyl-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4(4aH)-one (7.6 g, 26.6 mmol) in 1,2-dichloroethane (20 mL, anhydrous) and were stirred in a preheated oil bath at 90° C. for 1 hr. Reaction mixture was poured into ice, neutralized by solid sodium carbonate, extracted by ethyl acetate and dried over sodium sulfate. Solvent was removed in vacuo and light brown oil residue was used directly in the next step.

Workup

  1. customReaction mixture
  2. additionwas poured into ice
  3. extractionextracted by ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. customSolvent was removed in vacuo and light brown oil residue

Sources & evidence

ORD record
ord-88ed64c634f4485a81d4a7b5b1f5b050
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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