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

HRID 2067740ノート

反応式

HRID 2067740 の反応式
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]

参加物

3

反応物 2

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

生成物 1

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

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-db93c2efbc1742b18de6f6c4880e4a2a
出典データセット
uspto-grants-2012_10
特許番号
US08293901B2

反応ノート

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