Sodium hydride → HCID 21865285, compound

HRID 858978Notes

Reaction equation

HRID 858978 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15](Cl)[N:14]=[CH:13][N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:18][O:19][C:20]1[CH:21]=[C:22]([SH:26])[CH:23]=[CH:24][CH:25]=1.[H-].[Na+]>CN(C=O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[C:15]([S:26][C:22]3[CH:23]=[CH:24][CH:25]=[C:20]([O:19][CH3:18])[CH:21]=3)[N:14]=[CH:13][N:12]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 849893-MethoxybenzenethiolHCID 16749212HCID 16749212, compound

Product 1

HCID 21865285HCID 21865285, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 25-mL, round-bottomed flask containing 4-(4-tert-butyl-phenyl)-6-chloro-pyrimidine, (Example 1(a)), (0.20 g, 0.82 mmol), 3-methoxybenzenethiol (0.23 g, 1.6 mmol, Aldrich) and DMF (4 mL) under a N2 atmosphere at room temperature was added NaH (0.066 g, 1.6 mmol, 60% disp. in oil, Aldrich). The mixture turned green and gas evolution was observed. The solution was stirred for 20 h at room temperature under a N2 atmosphere. The reaction was quenched with H2O (50 mL), and the resulting solution was extracted with EtOAc (3×25 mL). The combined extracts were washed with H2O (3×25 mL) and brine, dried over Na2SO4, and adsorbed onto silica. The crude material was purified by chromatography (0 to 15% ethyl acetate/hexanes) on silica gel to afford the title compound as a colorless oil. MS (ESI, pos. ion.) m/z: 351.2 (M+1).

Workup

  1. customThe reaction was quenched with H2O (50 mL)
  2. extractionthe resulting solution was extracted with EtOAc (3×25 mL)
  3. washThe combined extracts were washed with H2O (3×25 mL) and brine
  4. dry with materialdried over Na2SO4
  5. customThe crude material was purified by chromatography (0 to 15% ethyl acetate/hexanes) on silica gel

Sources & evidence

ORD record
ord-e0c8581cdcef41aea1a0b28956cb883c
Source dataset
uspto-grants-2006_12
Patent number
US07148221B2

Reaction notes

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