Acetic Acid → 4-benzyl-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-methyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

HRID 1930633ノート

反応式

HRID 1930633 の反応式
[CH2:1]([C:8]1[C:9]2[CH2:32][NH:31][CH2:30][CH2:29][C:10]=2[N:11]=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22]3)=[C:17]([O:27][CH3:28])[CH:16]=2)[N:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:33](O)(=O)C.C=O.C([BH3-])#N.[Na+]>CO>[CH2:1]([C:8]1[C:9]2[CH2:32][N:31]([CH3:33])[CH2:30][CH2:29][C:10]=2[N:11]=[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH:25]=[C:24]([CH3:26])[N:23]=[CH:22]3)=[C:17]([O:27][CH3:28])[CH:16]=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 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 593336984-Benzyl-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine

生成物 1

HCID 461994304-benzyl-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-methyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine収率 17.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

4-Benzyl-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (400 mg, 0.94 mmol, example 106) was is dissolved in methanol (5 mL). Acetic acid (0.054 mL, 0.94 mmol) was added followed by formaldehyde (0.070 mL, 0.94 mmol). The reaction mixture was stirred at room temperature for 15 minutes and sodium cyanoborohydride (58.9 mg, 0.94 mmol) was added. LCMS analysis showed full conversion after 1 h. The solvent was evaporated under reduced pressure, the crude redissolved in methanol, filtered and purified by preparative HPLC yielding 4-benzyl-N-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-6-methyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (74.0 mg, 17.60%). MS (ES+) m/z 441.3 (M+H)+

後処理

  1. customafter 1 h
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe crude redissolved in methanol
  4. filtrationfiltered
  5. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-e1963bf072964e88974e9792f5ad3c66
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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