Acetic Acid → 2-(4-benzyl-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanol

HRID 1930590ノート

反応式

HRID 1930590 の反応式
[CH2:1]([C:8]1[C:9]2[CH2:30][NH:29][CH2:28][CH2:27][C:10]=2[N:11]=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:25]=[CH:24][N:23]=[C:22]3[CH3:26])=[CH:17][CH:16]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31](O)(=[O:33])[CH3:32].C(O)C=O.C([BH3-])#N.[Na+]>CO>[CH2:1]([C:8]1[C:9]2[CH2:30][N:29]([CH2:32][CH2:31][OH:33])[CH2:28][CH2:27][C:10]=2[N:11]=[C:12]([NH:14][C:15]2[CH:16]=[CH:17][C:18]([N:21]3[CH:25]=[CH:24][N:23]=[C:22]3[CH3:26])=[CH:19][CH:20]=2)[N:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 756GlycolaldehydeHCID 5003444Sodium cyanoborohydrideHCID 593336944-Benzyl-N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

生成物 1

HCID 461986572-(4-benzyl-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanol収率 21.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

4-Benzyl-N-(4-(2-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (75 mg, 0.19 mmol) was dissolved in methanol (2 mL). Acetic acid (10.83 μL, 0.19 mmol) was added followed by glycoaldehyde (11.36 mg, 0.19 mmol) and sodium cyanoborohydride (11.89 mg, 0.19 mmol). The reaction mixture was stirred at room temperature for 1 h and the solvent was evaporated under reduced pressure. The crude was dissolved in methanol, filtered and purified by preparative HPLC yielding 2-(4-benzyl-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanol (18.10 mg, 19.7%). MS (ES+) (M+H)+=441.3

後処理

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe crude was dissolved in methanol
  3. filtrationfiltered
  4. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-a83ad734854848f498216a09b7b0203a
出典データセット
uspto-grants-2012_05
特許番号
US08188101B2

反応ノート

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