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 1930590Notes

Reaction equation

HRID 1930590 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-a83ad734854848f498216a09b7b0203a
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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