Triphenyl phosphite → Methyl 4-methyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-7-carboxylate

HRID 716269

反応式

HRID 716269 の反応式
C[O:2][C:3](=O)[CH2:4][N:5]([CH3:19])[C:6]1[C:15]([N+:16]([O-])=O)=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][N:7]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[H][H]>ClCCl.[NH4+].[O-][V](=O)=O.[Pt]>[CH3:19][N:5]1[CH2:4][C:3](=[O:2])[NH:16][C:15]2[CH:14]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[CH:8]=[N:7][C:6]1=2

参加物

7

反応物 3

HCID 7540Triphenyl phosphiteHCID 58324470Methyl 6-((2-methoxy-2-oxoethyl)(methyl)amino)-5-nitronicotinateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 58324455Methyl 4-methyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-b]pyrazine-7-carboxylate収率 68.8%

試薬・触媒・溶媒 3

HCID 23939Platinum触媒HCID 516859Ammonium metavanadate触媒HCID 6344Dichloromethane溶媒2 回

実験手順

Methyl 6-((2-methoxy-2-oxoethyl)(methyl)amino)-5-nitronicotinate (2.7 g, 9.53 mmol) was dissolved in dichloromethane (10 mL). To the yellow solution was added ammonium metavanadate (30.0 mg, 0.256 mmol), triphenyl phosphite (aprox 30 ul, 0.097 mmol), and Pt/C (300 mg, 5% w/w). The reaction mixture was pressurized with hydrogen gas (110 psi) and stirred at room temperature for 16 h. The reaction was then depressurized and diluted with dichloromethane (100 mL) which was then refluxed for 30 min. The hot solution was filtered through a pad of celite and washed with hot dichloromethane (3×20 mL). The filtrate was concentrated in vacuo to yield the title compound (1.45 g, 68%) as a white solid. [M+H] calc'd for C10H11N3O3, 222. found, 222.

後処理

  1. temperaturewas then refluxed for 30 min
  2. filtrationThe hot solution was filtered through a pad of celite
  3. washwashed with hot dichloromethane (3×20 mL)
  4. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-fe21c1d1f92845fea14941378afd5ec2
出典データセット
uspto-grants-2015_11
特許番号
US09187497B2

関連ノート

読み込み中…