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 1930590노트

반응식

HRID 1930590 반응식
[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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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

후처리

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

출처 및 근거

ORD 기록
ord-a83ad734854848f498216a09b7b0203a
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08188101B2

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