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Acetic Acid → 2-((2-(4-(Oxazol-5-yl)phenylamino)-6-propyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol

HRID 1930558
Notes
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Reaction equation

HRID 1930558 reaction equation
[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]3[N:14]=[C:15]([N:23]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:24][CH2:25][OH:26])[C:16]4[CH2:22][NH:21][CH2:20][CH2:19][C:17]=4[N:18]=3)=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1.C(O)(=O)C.[CH:37](=O)[CH2:38][CH3:39].C([BH3-])#N.[Na+]>CO>[O:1]1[C:5]([C:6]2[CH:11]=[CH:10][C:9]([NH:12][C:13]3[N:14]=[C:15]([N:23]([C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH2:24][CH2:25][OH:26])[C:16]4[CH2:22][N:21]([CH2:37][CH2:38][CH3:39])[CH2:20][CH2:19][C:17]=4[N:18]=3)=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 5003444Sodium cyanoborohydrideHCID 462000502-((2-(4-(Oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol

Product 1

HCID 462003542-((2-(4-(Oxazol-5-yl)phenylamino)-6-propyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanolYield 22.95%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-((2-(4-(Oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol (25 mg, 0.06 mmol, Example 1) was dissolved in methanol (1 mL). Acetic acid (0.013 mL, 0.23 mmol) and propionaldehyde (4.25 μL, 0.06 mmol) was added and the reaction mixture was stirred at room temperature for 10 minutes. Sodium cyanoborohydride (3.67 mg, 0.06 mmol) was added and after 15 minutes the solvent was evaporated under reduced pressure. The crude was dissolved in few drops of dimethylformamide and acetonitrile, filtered and purified by preparative HPLC yielding 2-((2-(4-(oxazol-5-yl)phenylamino)-6-propyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol (6.3 mg, 22.95%).

Workup

  1. customwas evaporated under reduced pressure
  2. dissolutionThe crude was dissolved in few drops of dimethylformamide and acetonitrile
  3. filtrationfiltered
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-00d4f4d907a743ecb22262bd02ed324b
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08188101B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes