Acetic Acid → 2-(2-(4-(oxazol-5-yl)phenylamino)-4-((tetrahydro-2H-pyran-4-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanol

HRID 1930676Notes

Reaction equation

HRID 1930676 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]([NH:23][CH2:24][CH:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[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:31](O)(=[O:33])[CH3:32].C(O)C=O>CO>[O:1]1[C:5]([C:6]2[CH:7]=[CH:8][C:9]([NH:12][C:13]3[N:14]=[C:15]([NH:23][CH2:24][CH:25]4[CH2:26][CH2:27][O:28][CH2:29][CH2:30]4)[C:16]4[CH2:22][N:21]([CH2:32][CH2:31][OH:33])[CH2:20][CH2:19][C:17]=4[N:18]=3)=[CH:10][CH:11]=2)=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 756GlycolaldehydeHCID 59333782N2-(4-(Oxazol-5-yl)phenyl)-N4-((tetrahydro-2H-pyran-4-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine

Product 1

HCID 593337652-(2-(4-(oxazol-5-yl)phenylamino)-4-((tetrahydro-2H-pyran-4-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanolYield 25.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N2-(4-(Oxazol-5-yl)phenyl)-N4-((tetrahydro-2H-pyran-4-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamine (134 mg, 0.33 mmol, example 85a) was dissolved in methanol (3 mL). Acetic acid (0.019 mL, 0.33 mmol) was added followed by glycoaldehyde (19.80 mg, 0.33 mmol). The reaction mixture was stirred at room temperature for 15 minutes and MP—CNBH3 was added. The reaction mixture was stirred overnight, the MP—CNBH3 was filtered off, the solvent was evaporated under reduced pressure, the crude was purified twice by HPLC yielding 2-(2-(4-(oxazol-5-yl)phenylamino)-4-((tetrahydro-2H-pyran-4-yl)methylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)ethanol (38.0 mg, 22.58%) as acetate salt. MS (ES+) m/z 451.3 (M+H)+

Workup

  1. additionMP—CNBH3 was added
  2. stirringThe reaction mixture was stirred overnight
  3. filtrationthe MP—CNBH3 was filtered off
  4. customthe solvent was evaporated under reduced pressure
  5. customthe crude was purified twice by HPLC

Sources & evidence

ORD record
ord-54e549229f40400a8cbd3df7230b4d8f
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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