Methyl chloroformate → methyl 4-((2-hydroxyethyl)(phenyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 1930567Notes

Reaction equation

HRID 1930567 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.Cl[C:34]([O:36][CH3:37])=[O:35]>CN(C=O)C>[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:34]([O:36][CH3:37])=[O:35])[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

4

Reactant 2

HCID 6586Methyl chloroformateHCID 462000502-((2-(4-(Oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol

Product 1

HCID 46200668methyl 4-((2-hydroxyethyl)(phenyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylateYield 30.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-((2-(4-(Oxazol-5-yl)phenylamino)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)(phenyl)amino)ethanol (80 mg, 0.19 mmol, Example 1) was dissolved in DMF (5 mL). Methyl chloroformate (0.014 mL, 0.19 mmol) was added and the reaction was stirred for 2 h. The solvent was evaporated, the crude dissolved in few drops of dimethylformamide and acetonitrile, filtered and purified by HPLC. The fractions containing the title compound were pulled together and freezed-dried overnight, yielding methyl 4-((2-hydroxyethyl)(phenyl)amino)-2-(4-(oxazol-5-yl)phenylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (28.0 mg, 30.8%).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe crude dissolved in few drops of dimethylformamide and acetonitrile
  3. filtrationfiltered
  4. custompurified by HPLC
  5. additionThe fractions containing the title compound
  6. customfreezed-dried overnight

Sources & evidence

ORD record
ord-b9af5d90583d48a89f151402b3b3416c
Source dataset
uspto-grants-2012_05
Patent number
US08188101B2

Reaction notes

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