Ethanolamine → HCID 59639624, compound

HRID 2250056Notes

Reaction equation

HRID 2250056 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:21]=[CH:20][C:19](=[O:22])[N:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH3:29])[C:10]=3[N:11]=[C:12](S(C)(=O)=O)[N:13]=2)=[C:4]([CH3:30])[CH:3]=1.[CH2:31]([CH2:33][NH2:34])[OH:32].O.CN1[C:41](=[O:42])CCC1>CCOC(C)=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[CH:21]=[CH:20][C:19](=[O:22])[N:18]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH3:29])[C:10]=3[N:11]=[C:12]([NH:34][CH:33]([CH2:41][OH:42])[CH2:31][OH:32])[N:13]=2)=[C:4]([CH3:30])[CH:3]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 962WaterHCID 13387N-methyl-2-pyrrolidoneHCID 59639608HCID 59639608, compound

Product 1

HCID 59639624HCID 59639624, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 121 (400 mg, 0.95 mmol) and ethanolamine (0.29 mL, 4.73 mmol) in NMP (2 mL) was stirred at 23° for 1 h. The mixture was diluted with EtOAc, washed with H2O, the organic phase was separated, EtOAc was removed in vacuo and the residue was purified by Flash chromatography on silica gel, eluting with EtOAc/hexane/triethylamine (50/50/2, v/v/v), followed by evaporation of solvent to afford a gummy residue. Trituration with H2O, gave the title compound compound 4-(4-fluoro-2-methyl-phenyl)-2-(2-hydroxy-1-hydroxymethyl-ethylamino)-8-ortho-tolyl-8H-pyrido[2,3-d]pyrimidin-7-one as a white solid (340 mg, 88%). LC-MS: 405.4 (MH+, m/z), Rt=1.85 min.

Workup

  1. washwashed with H2O
  2. customthe organic phase was separated
  3. customEtOAc was removed in vacuo
  4. customthe residue was purified by Flash chromatography on silica gel
  5. washeluting with EtOAc/hexane/triethylamine (50/50/2, v/v/v)
  6. customfollowed by evaporation of solvent
  7. customto afford a gummy residue

Sources & evidence

ORD record
ord-fcf818365afd44d898d571e6c7de4526
Source dataset
uspto-grants-2008_01
Patent number
US07314934B2

Reaction notes

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