2-methylsulfinyl-6-(3,5-dimethoxy-phenyl)8-ethyl-8H-pyrido[2,3-d]pyrimidine-7-one → 6-(3,5-Dimethoxy-phenyl)-2-(2,6-dimethoxy-pyridin-4-ylamino)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 1793884노트

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HRID 1793884 반응식
[NH2:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([O:10][CH3:11])[CH:3]=1.C([Li])CCC.[CH3:17][O:18][C:19]1[CH:20]=[C:21]([C:27]2[C:39](=[O:40])[N:38]([CH2:41][CH3:42])[C:30]3[N:31]=[C:32](S(C)=O)[N:33]=[CH:34][C:29]=3[CH:28]=2)[CH:22]=[C:23]([O:25][CH3:26])[CH:24]=1.C(OCC)(=O)C.O>C1COCC1>[CH3:26][O:25][C:23]1[CH:22]=[C:21]([C:27]2[C:39](=[O:40])[N:38]([CH2:41][CH3:42])[C:30]3[N:31]=[C:32]([NH:1][C:2]4[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([O:10][CH3:11])[CH:3]=4)[N:33]=[CH:34][C:29]=3[CH:28]=2)[CH:20]=[C:19]([O:18][CH3:17])[CH:24]=1

참가 물질

6

반응물 4

HCID 222201672-methylsulfinyl-6-(3,5-dimethoxy-phenyl)8-ethyl-8H-pyrido[2,3-d]pyrimidine-7-oneHCID 222201912,6-Dimethoxypyridin-4-amineHCID 22728543Water ethylacetateHCID 178418339Butyllithium

생성물 1

HCID 222201756-(3,5-Dimethoxy-phenyl)-2-(2,6-dimethoxy-pyridin-4-ylamino)-8-ethyl-8H-pyrido[2,3-d]pyrimidin-7-one수율 51%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-10 °C

실험 절차

To a −78° C. solution of 3.0 g (19.5 mmol) of 4-amino-2,6-dimethoxypyridine in 75 mL of THF was added dropwise 10.6 mL (17.0 mmol) of 1.6 M n-butyllithium in hexanes. The reaction solution was stirred for 15 minutes at which time 1.8 g (4.9 mmol) of 6-(3,5-dimethoxy-phenyl)-8-ethyl-2-methylsulfinyl-8H-pyrido[2,3-d]pyrimidin-7-one was added in small portions as a solid. The reaction mixture was allowed to warm slowly to −10° C. then remain at −10° C. overnight. The reaction mixture was poured into ethyl acetate/water/3.5 mL 6N HCl. The mixture is shaken and separated. The organic phase was washed with a saturated solution of sodium bicarbonate, twice with water, and brine, then dried over magnesium sulfate, filtered, and concentrated to a solid yellow residue. The solid was triturated under 25 mL of 1:15:10 methanol/chloroform/ethyl acetate and filtered to give a yellow solid that is crystallized from 300 mL of acetonitrile to give 1.15 g (51%) of the titled compound.

후처리

  1. additionwas added in small portions as a solid
  2. customseparated
  3. washThe organic phase was washed with a saturated solution of sodium bicarbonate, twice with water, and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a solid yellow residue
  7. customThe solid was triturated under 25 mL of 1:15:10 methanol/chloroform/ethyl acetate
  8. filtrationfiltered
  9. customto give a yellow solid
  10. customthat is crystallized from 300 mL of acetonitrile

출처 및 근거

ORD 기록
ord-8b25f207885843d192eaf1ed8df8ac71
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07022711B2

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