Phosphorus oxychloride → 3-Benzyl-5-chloro-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 1260425Notes

Reaction equation

HRID 1260425 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15](O)=[CH:16][C:17](=[O:20])[N:18]([CH3:19])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O=P(Cl)(Cl)[Cl:24]>>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]([Cl:24])=[CH:16][C:17](=[O:20])[N:18]([CH3:19])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 598230373-Benzyl-5-hydroxy-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

Product 1

HCID 598230573-Benzyl-5-chloro-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dioneYield 94%

Procedure

3-Benzyl-5-hydroxy-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (1.1 g, 3.88 mmol) was dissolved in excess POCl3 (5 mL) and subjected to microwave irradiation at 70° C. for 30 minutes. The POCl3 was removed in vacuo and the residue dissolved in DCM then quickly washed with saturated sodium bicarbonate solution until neutral pH was observed. The organic layer was dried over MgSO4 and evaporated to dryness to give 1.5 g of the title compound as a reddish brown solid (94%). [M+H] calc'd for C15H12ClN3O, 302. found, 302.

Workup

  1. customirradiation at 70° C. for 30 minutes
  2. customThe POCl3 was removed in vacuo
  3. dissolutionthe residue dissolved in DCM
  4. washthen quickly washed with saturated sodium bicarbonate solution until neutral pH
  5. dry with materialThe organic layer was dried over MgSO4
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-6a1e6a59ef924f8ba5feb4b551ac399e
Source dataset
uspto-grants-2013_06
Patent number
US08470837B2

Reaction notes

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