Phosphorus oxychloride → 4-Chloro-6-(N,N-dimethylamino)-pyrido[3,4-d]pyrimidine

HRID 2085941Notes

Reaction equation

HRID 2085941 reaction equation
[CH3:1][N:2]([C:4]1[N:14]=[CH:13][C:7]2[N:8]=[CH:9][NH:10][C:11](=O)[C:6]=2[CH:5]=1)[CH3:3].P(Cl)(Cl)([Cl:17])=O>C(N(CC)CC)C>[Cl:17][C:11]1[C:6]2[CH:5]=[C:4]([N:2]([CH3:3])[CH3:1])[N:14]=[CH:13][C:7]=2[N:8]=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1358174466-(N,N-Dimethylamino)-3H-pyrido[3,4-d]pyrimidin-4-one

Product 1

HCID 227274534-Chloro-6-(N,N-dimethylamino)-pyrido[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

6-(N,N-Dimethylamino)-pyrido[3,4-d]pyrimidin-4-one (12 g) was carefully treated with phosphorus oxychloride (42 ml) and triethylamine (18 ml) at room temperature under N2. After 1 hour at room temperature and 1 hour at 50° C., the mixture was concentrated in vacuo, azeotroping with toluene, then taken up in ethyl acetate, washed with sodium bicarbonate solution, dried and concentrated in vacuo to give the title compound (10.34 g); δH CDCl3 9.13(1H,s), 8.74(1H,s), 6.69(1H,s), 3.25(6H,s).

Workup

  1. concentration1 hour at 50° C., the mixture was concentrated in vacuo
  2. customazeotroping with toluene
  3. washwashed with sodium bicarbonate solution
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de45c3c46961433b9aa7b231a5a084d4
Source dataset
uspto-grants-2004_04
Patent number
US06723726B1

Reaction notes

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