Triethylamine → HCID 57877935, compound

HRID 1091394Notes

Reaction equation

HRID 1091394 reaction equation
Cl.[CH3:2][N:3]([CH3:16])[C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]2[O:15][CH2:14][CH2:13][NH:12][CH2:11]2)=[CH:6][CH:5]=1.Cl[C:18]1[N:19]([CH3:32])[C:20](=[O:31])[CH:21]=[C:22]([C:24]2[CH:29]=[CH:28][N:27]=[CH:26][C:25]=2[F:30])[N:23]=1.C(N(CC)CC)C>O1CCCC1>[CH3:2][N:3]([CH3:16])[C:4]1[CH:5]=[CH:6][C:7]([C@@H:10]2[O:15][CH2:14][CH2:13][N:12]([C:18]3[N:19]([CH3:32])[C:20](=[O:31])[CH:21]=[C:22]([C:24]4[CH:29]=[CH:28][N:27]=[CH:26][C:25]=4[F:30])[N:23]=3)[CH2:11]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 595768122-Chloro-3-methyl-6-(3-fluoropyridin-4-yl)-3H-pyrimidin-4-oneHCID 66594953HCID 66594953, compound

Product 1

HCID 57877935HCID 57877935, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (2S)-2-(4-(dimethylamino)phenyl)morpholine hydrochloride (0.20 g, 0.64 mmol), 2-chloro-1-methyl-6-oxo-4-(3-fluoropyridin-4-yl)-1,6-dihydropyrimidine (0.12 g, 0.53 mmol), and triethylamine (0.19 g, 1.92 mmol) in tetrahydrofuran (10 ml) was stirred at 95° C. for 3 hours. The solvent was evaporated off in vacuo and the residue treated with water and dichloromethane. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (chloroform-methanol, 10:1) to afford 2-((2S)-2-(4-(dimethylamino)phenyl)morpholin-4-yl)-6-(3-fluoropyridin-4-yl)-3-methyl-3H-pyrimidin-4-one (0.10 g, 50%) as yellow crystals

Workup

  1. customThe solvent was evaporated off in vacuo
  2. additionthe residue treated with water and dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by column chromatography on silica gel (chloroform-methanol, 10:1)

Sources & evidence

ORD record
ord-c816ff9c833c47eb8cbb272dc95cb257
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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