Phosphorus oxychloride → 5-Chloro-3-(4-methoxybenzyl)-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 1260431Notes

Reaction equation

HRID 1260431 reaction equation
O[C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH:8]=[N:7][C:6]=2[N:5]([CH3:22])[C:4](=[O:23])[C:3]=1[CH3:24].P(Cl)(Cl)([Cl:27])=O>>[Cl:27][C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[CH:8]=[N:7][C:6]=2[N:5]([CH3:22])[C:4](=[O:23])[C:3]=1[CH3:24]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 598230495-Hydroxy-3-(4-methoxybenzyl)-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione2×

Product 1

HCID 593344495-Chloro-3-(4-methoxybenzyl)-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dioneYield 89%

Conditions

Temperature
80 °C

Procedure

5-Hydroxy-3-(4-methoxybenzyl)-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (10 g, 30.6 mmol, compound 8B) was suspended in phosphorus oxychloride (28 mL, 306 mmol) and heated at 80° C. for 5 hours. The solution was evaporated in vacuo, and the residue taken up in DCM and washed with saturated sodium bicarbonate solution until the neutral pH was observed. The organic layer was dried over magnesium sulfate and evaporated to dryness. The residue was purified by silica chromatography using 1% methanol in DCM as eluent to yield 9.28 g of title compound (89%). [M+H] calc'd for C17H16ClN3O3, 346. found, 346.

Workup

  1. customThe solution was evaporated in vacuo
  2. washwashed with saturated sodium bicarbonate solution until the neutral pH
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-1f00c5551c164d09a0bb09d569eb64db
Source dataset
uspto-grants-2013_06
Patent number
US08470837B2

Reaction notes

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