Acetic Acid → HCID 46200200, compound

HRID 1930549Notes

Reaction equation

HRID 1930549 reaction equation
[C:1]([OH:4])(=O)[CH3:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([NH:19][C:20]2[N:21]=[C:22]([NH:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:23]3[CH2:29][NH:28][CH2:27][CH2:26][C:24]=3[N:25]=2)[CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]1.OCC=O.C([BH3-])#N.[Na+]>CO>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([NH:19][C:20]2[N:21]=[C:22]([NH:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:23]3[CH2:29][N:28]([CH2:2][CH2:1][OH:4])[CH2:27][CH2:26][C:24]=3[N:25]=2)[CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 756GlycolaldehydeHCID 5003444Sodium cyanoborohydrideHCID 46200199HCID 46200199, compound

Product 1

HCID 46200200HCID 46200200, compoundYield 381.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetic acid (0.803 μL, 0.01 mmol) was added to a solution of N2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-N4-phenyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (Example 7, 0.03 g, 0.07 mmol) and 2-hydroxyacetaldehyde (4.21 mg, 0.07 mmol) in MeOH (5 mL). The reaction mixture was stirred for 10 min and sodium cyanoborohydride (4.41 mg, 0.07 mmol) added. The reaction was stirred for an additional 15 min and solvent evaporated under reduced pressure. The crude product was dissolved in MeOH/DMSO and purified by preparative HPLC to give 2-(2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-4-(phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanol (0.018 g, 53.5%). MS (ESI+)/(ESI−) m/z 472/470

Workup

  1. stirringThe reaction was stirred for an additional 15 min
  2. customsolvent evaporated under reduced pressure
  3. dissolutionThe crude product was dissolved in MeOH/DMSO
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-9d17d74037124e7f984735305bf28dbd
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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