Benzylamine → HCID 59333754, compound

HRID 1930541Notes

Reaction equation

HRID 1930541 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:9]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]3[N:22]=[C:23](OS(C(F)(F)F)(=O)=O)[C:24]4[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][C:25]=4[N:26]=3)=[CH:16][CH:15]=2)=[CH:12][N:11]=[CH:10]1>O1CCOCC1.CN(C=O)C>[CH2:1]([NH:8][C:23]1[C:24]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][C:25]=2[N:26]=[C:21]([NH:20][C:17]2[CH:16]=[CH:15][C:14]([C:13]3[O:9][CH:10]=[N:11][CH:12]=3)=[CH:19][CH:18]=2)[N:22]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7504BenzylamineHCID 59333781HCID 59333781, compound

Product 1

HCID 59333754HCID 59333754, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

Benzylamine (0.030 g, 0.28 mmol) was added to tert-butyl 2-(4-(oxazol-5-yl)phenylamino)-4-(trifluoromethylsulfonyloxy)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate (0.15 g, 0.28 mmol, Example 5b) in dioxane (10 mL) and DMF (0.5 mL). The reaction was stirred at rt over night. The solvent was removed under reduced pressure and the crude product redissolved in EtOAc, washed with saturated NaHCO3 and H2O. The organic layer was dried (MgSO4), filtered and concentrated to give tert-butyl 4-(benzylamino)-2-(4-(oxazol-5-yl)phenylamino)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate (0.120 g, 87%). No further purification.

Workup

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe crude product redissolved in EtOAc
  3. washwashed with saturated NaHCO3 and H2O
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-aca4519bea864af9b2b5efe215aafaeb
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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