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Acetic Acid → 2-(4-(ethyl((tetrahydrofuran-2-yl)methyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanol

HRID 1930665
Notes
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Reaction equation

HRID 1930665 reaction equation
[CH2:1]([N:3]([CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][O:28]1)[C:4]1[C:5]2[CH2:25][NH:24][CH2:23][CH2:22][C:6]=2[N:7]=[C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[O:21][CH:20]=[N:19][CH:18]=3)=[CH:13][CH:12]=2)[N:9]=1)[CH3:2].[C:32](O)(=[O:34])[CH3:33].C(O)C=O.C([BH3-])#N.[Na+]>CO>[CH2:1]([N:3]([CH2:26][CH:27]1[CH2:31][CH2:30][CH2:29][O:28]1)[C:4]1[C:5]2[CH2:25][N:24]([CH2:33][CH2:32][OH:34])[CH2:23][CH2:22][C:6]=2[N:7]=[C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([C:17]3[O:21][CH:20]=[N:19][CH:18]=3)=[CH:15][CH:16]=2)[N:9]=1)[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 756GlycolaldehydeHCID 5003444Sodium cyanoborohydrideHCID 59333759N4-Ethyl-N2-(4-(oxazol-5-yl)phenyl)-N4-((tetrahydrofuran-2-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine

Product 1

HCID 461997412-(4-(ethyl((tetrahydrofuran-2-yl)methyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanol
Yield 38.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N4-Ethyl-N2-(4-(oxazol-5-yl)phenyl)-N4-((tetrahydrofuran-2-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (125 mg, 0.30 mmol) was dissolved in methanol (3 mL). Acetic acid (0.017 mL, 0.30 mmol) was added followed by glycoaldehyde (17.85 mg, 0.30 mmol). The reaction mixture was stirred for 15 minutes at room temperature and sodium cyanoborohydride (18.68 mg, 0.30 mmol) (MP—CNBH3) was added. The reaction was stirred overnight at room temperature, the MP—CNBH3 was filtered off, the solvent was evaporated under reduced pressure and the crude was purified by preparative HPLC yielding 2-(4-(ethyl((tetrahydrofuran-2-yl)methyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanol (54.0 mg, 34.6%) as acetate salt. MS (ES+) m/z 465.3 (M+H)+

Workup

  1. stirringThe reaction was stirred overnight at room temperature
  2. filtrationthe MP—CNBH3 was filtered off
  3. customthe solvent was evaporated under reduced pressure
  4. customthe crude was purified by preparative HPLC

Sources & evidence

ORD record
ord-a086a588550b47f0ae6659fc0ff0af91
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