Triethylamine → (2-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)(pyridin-3-yl)methanone

HRID 930496노트

반응식

HRID 930496 반응식
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[Cl:10][C:11]1[N:12]=[CH:13][C:14]2[CH2:20][NH:19][CH2:18][CH2:17][C:15]=2[N:16]=1.C(N(CC)CC)C>C1COCC1>[Cl:10][C:11]1[N:12]=[CH:13][C:14]2[CH2:20][N:19]([C:1]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=3)=[O:8])[CH2:18][CH2:17][C:15]=2[N:16]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 82604Nicotinoyl chlorideHCID 223084842-Chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

생성물 1

HCID 118970896(2-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)(pyridin-3-yl)methanone수율 87.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of nicotinoyl chloride (0.230 g, 1.62 mmol) in anhydrous THF (1.5 mL) was treated with 2-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (0.250 g, 1.47 mmol) and triethylamine (0.3 g, 3.0 mmol) and subsequently allowed to stir at room temperature. After 4 hours the reaction was quenched with deionized H2O (10 mL). Following dilution with EtOAc (10 mL) the reaction mixture was washed twice with brine and once with saturated Na2HCO3(aq). The combined aqueous layers were then washed once with EtOAc. The combined organic layers were dried over anhydrous Na2SO4(s), filtered and then concentrated in vacuo. Purification over silica using a Methanol/CHCl3 gradient afforded the desired product in 87.9% yield (0.356 g, 1.3 mmol).

후처리

  1. customAfter 4 hours the reaction was quenched with deionized H2O (10 mL)
  2. washwas washed twice with brine and once with saturated Na2HCO3(aq)
  3. washThe combined aqueous layers were then washed once with EtOAc
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4(s)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification over silica using a Methanol/CHCl3

출처 및 근거

ORD 기록
ord-3015f49062104a2380440d20d6312900
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296747B1

반응 노트

불러오는 중…