4-Methylpyrimidine → HCID 136375617, compound

HRID 1296705

Reaction equation

HRID 1296705 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][N:3]=1.[Cl:8][C:9]1[CH:10]=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12](OCC)=[O:13].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>O1CCCC1>[Cl:8][C:9]1[CH:10]=[C:11]([C:12]([OH:13])=[CH:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][N:3]=2)[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 189224-MethylpyrimidineHCID 70785Ethyl 3-chlorobenzoateHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 136375617HCID 136375617, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (0° C.) solution of 4-methylpyrimidine (4.56 mL 50.1 mmol) and ethyl 3-chlorobenzoate (7.90 mL 50.1 mmol) in tetrahydrofuran (50 mL) was added lithium bis(trimethylsilyl)amide (100 mL, 1.0M in tetrahydrofuran, 100 mmol) dropwise over 30 minutes. The resultant mixture was warmed to room temperature and stirred 16 hours. The reaction mixture was concentrated in vacuo. The resultant oil was diluted with methanol. Upon standing, a solid precipitated, which was collected on a filter to provide 1-(3-chlorophenyl)-2-(4-pyrimidinyl)ethenol (11.2 g, 93%) as a yellow solid. Rf 0.31 (3:1 hexanes:ethyl acetate); 1H NMR (d6-DMSO) δ 8.37 (s, 1H), 7.98 (m, 1H), 7.81–7.76 (m, 2H), 7.38–7.32 (m, 2H), 6.71 (br, 1H), 5.65 (s, 1H); MS m/z 233 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionThe resultant oil was diluted with methanol
  3. customa solid precipitated
  4. customwhich was collected on
  5. filtrationa filter

Sources & evidence

ORD record
ord-e771dfcbc4ea444089d4ba7654147751
Source dataset
uspto-grants-2007_07
Patent number
US07247626B2

Linked notes

Loading…