Dimethylcarbamoyl Chloride → 4-((2-hydroxyethyl)(phenyl)amino)-N,N-dimethyl-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxamide

HRID 1930569Notes

Reaction equation

HRID 1930569 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(N(CC)CC)C.[CH3:40][N:41]([CH3:45])[C:42](Cl)=[O:43]>ClCCl.CO>[OH:26][CH2:25][CH2:24][N:23]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[C:15]1[C:16]2[CH2:22][N:21]([C:42]([N:41]([CH3:45])[CH3:40])=[O:43])[CH2:20][CH2:19][C:17]=2[N:18]=[C:13]([NH:12][C:9]2[CH:10]=[CH:11][C:6]([C:5]3[O:1][CH:2]=[N:3][CH:4]=3)=[CH:7][CH:8]=2)[N:14]=1

Participants

6

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 8471TriethylamineHCID 462000502-((2-(4-(Oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol

Product 1

HCID 462006704-((2-hydroxyethyl)(phenyl)amino)-N,N-dimethyl-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxamideYield 33%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

2-((2-(4-(Oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol (50 mg, 0.12 mmol, Example 1) was dissolved in dichloromethane (5 mL) and methanol (1 mL). Triethylamine (0.016 mL, 0.12 mmol) was added followed by dimethylcarbamyl chloride (10.72 μL, 0.12 mmol). The reaction mixture was stirred at room temperature for 2 h. The solvent was evaporated under reduced pressure, the crude dissolved in few drops of dimethylformamide and acetonitrile, filtered and purified by HPLC yielding 4-((2-hydroxyethyl)(phenyl)amino)-N,N-dimethyl-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxamide (19.0 mg, 33%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe crude dissolved in few drops of dimethylformamide and acetonitrile
  3. filtrationfiltered
  4. custompurified by HPLC

Sources & evidence

ORD record
ord-a64e999bc4854d77bb687f506868503e
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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