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

HRID 930496ノート

反応式

HRID 930496 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3015f49062104a2380440d20d6312900
出典データセット
uspto-grants-2016_03
特許番号
US09296747B1

反応ノート

読み込み中…