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

HRID 1930651Notes

Reaction equation

HRID 1930651 reaction equation
[CH2:1]([N:8]([C:12]1[C:13]2[CH2:34][NH:33][CH2:32][CH2:31][C:14]=2[N:15]=[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[CH:28][N:27]=[C:26]3[CH3:30])=[CH:21][CH:20]=2)[N:17]=1)[CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35](O)(=O)C.C=O.C([BH3-])#N.[Na+]>CO>[CH2:1]([N:8]([C:12]1[C:13]2[CH2:34][N:33]([CH3:35])[CH2:32][CH2:31][C:14]=2[N:15]=[C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH:29]=[CH:28][N:27]=[C:26]3[CH3:30])=[CH:21][CH:20]=2)[N:17]=1)[CH2:9][CH2:10][OH:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 593337392-(Benzyl(2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)amino)ethanol

Product 1

HCID 461995852-(benzyl(6-methyl-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)amino)ethanolYield 8.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(Benzyl(2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)amino)ethanol (95 mg, 0.21 mmol) was dissolved in methanol (3 mL). Acetic acid (0.012 mL, 0.21 mmol) was added followed by formaldehyde (0.016 mL, 0.21 mmol). The reaction mixture was stirred at room temperature for 15 minutes and sodium cyanoborohydride (13.10 mg, 0.21 mmol) was added. The solvent was evaporated after 1 h and the crude purified by preparative HPLC yielding 2-(benzyl(6-methyl-2-(4-(2-methyl-1H-imidazol-1-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)amino)ethanol (8.60 mg, 7.8%) as acetate salt. MS (ES+) m/z 470.3 (M+H)+

Workup

  1. customThe solvent was evaporated after 1 h
  2. customthe crude purified by preparative HPLC

Sources & evidence

ORD record
ord-925ab8b18dae46c0bdd06c4ccd4b3158
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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