N,N-Dimethylaniline → HCID 69221623, compound

HRID 971217Notes

Reaction equation

HRID 971217 reaction equation
C[N:2](C)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.P(Cl)(Cl)([Cl:12])=O.NC1N=[C:20]2[CH2:22][N:23]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:24]CC2C(=O)N=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCCl>[CH2:26]([N:23]1[CH2:22][CH2:20][C:6]2[C:5](=[CH:4][C:3]([NH2:2])=[CH:8][C:7]=2[Cl:12])[CH2:24]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 949N,N-DimethylanilineHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 69221023HCID 69221023, compound

Product 1

HCID 69221623HCID 69221623, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

N,N-Dimethylaniline (1.4 g, 11.4 mmol) and phosphorus oxychloride (14 g, 91.2 mmol) were added to a solution of 2-amino-7-benzyl-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4(4aH)-one (2.9 g, 11.4 mmol) in 1,2-dichloroethane (23 mL, anhydrous) and were stirred in a preheated oil bath at 90° C. for 45 min. The reaction mixture was poured into ice, neutralized by solid sodium carbonate, extracted by ethyl acetate, and the dark brown semi solid was dissolved in methanol. The combined ethyl acetate and methanol solution was dried over sodium sulfate. Solvent was removed in vacuo and product was obtained as a light brown solid (2.6 g).

Workup

  1. additionThe reaction mixture was poured into ice
  2. extractionextracted by ethyl acetate
  3. dissolutionthe dark brown semi solid was dissolved in methanol
  4. dry with materialThe combined ethyl acetate and methanol solution was dried over sodium sulfate
  5. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-818ae370e4cd4b5abd733daff298ce5d
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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