Acetic Acid → 6-methyl-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

HRID 1930673Notes

Reaction equation

HRID 1930673 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)C.C=O>CO>[CH3:31][N:21]1[CH2:20][CH2:19][C:17]2[N:18]=[C:13]([NH:12][C:9]3[CH:8]=[CH:7][C:6]([C:5]4[O:1][CH:2]=[N:3][CH:4]=4)=[CH:11][CH:10]=3)[N:14]=[C:15]([NH:23][CH2:24][CH:25]3[CH2:26][CH2:27][O:28][CH2:29][CH2:30]3)[C:16]=2[CH2:22]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 712FormaldehydeHCID 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 461998956-methyl-N2-(4-(oxazol-5-yl)phenyl)-N4-((tetrahydro-2H-pyran-4-yl)methyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine-2,4-diamineYield 16.6%

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) was dissolved in methanol (3 mL). Acetic acid (0.019 mL, 0.33 mmol) was added followed by formaldehyde (0.025 mL, 0.33 mmol). The reaction mixture was stirred at room temperature for 15 minutes and MP—CNBH3 was added. The reaction was stirred overnight. The MP—CNBH3 was filtered off and the solvent was evaporated under reduced pressure. The crude was dissolved in methanol, filtered and purified by HPLC yielding 6-methyl-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 (23.00 mg, 15.8%).

Workup

  1. additionMP—CNBH3 was added
  2. stirringThe reaction was stirred overnight
  3. filtrationThe MP—CNBH3 was filtered off
  4. customthe solvent was evaporated under reduced pressure
  5. dissolutionThe crude was dissolved in methanol
  6. filtrationfiltered
  7. custompurified by HPLC

Sources & evidence

ORD record
ord-3bfffb102bea474aa97b79846a354e5f
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

Loading…