Sodium hydride → 6-Phenyl-2-(4,6-dimethoxypyrimidin-2-yloxy)benzoic acid

HRID 1885986Notes

Reaction equation

HRID 1885986 reaction equation
[C:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([OH:16])[C:12]=2[C:13]([OH:15])=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:17][O:18][C:19]1[CH:24]=[C:23]([O:25][CH3:26])[N:22]=[C:21](S(C)(=O)=O)[N:20]=1.[H-].[Na+]>O1CCCC1>[C:1]1([C:7]2[C:12]([C:13]([OH:15])=[O:14])=[C:11]([O:16][C:21]3[N:22]=[C:23]([O:25][CH3:26])[CH:24]=[C:19]([O:18][CH3:17])[N:20]=3)[CH:10]=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidine2×HCID 156796253-Hydroxy-[1,1'-biphenyl]-2-carboxylic acid2×

Product 1

HCID 148806476-Phenyl-2-(4,6-dimethoxypyrimidin-2-yloxy)benzoic acidYield 160.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

This compound was prepared in a manner analogous to that of Example 5, Step D, using 0.5 gram (0.003 mole) of 6-phenylsalicylic acid, 0.6 gram (0.003 mole) of 4,6-dimethoxy-2-methylsulfonylpyrimidine, and 0.3 gram (0.005 mole) of 50% sodium hydride in mineral oil in 60 mL of tetrahydrofuran. This reaction mixture was combined with a second reaction mixture of 1.7 grams (0.008 mole) of 6-phenylsalicylic acid, 1.7 grams (.008 mole) of 4,6-dimethoxy-2-methylsulfonylpyrimidine and 0.8 gram (0.016 mole) of 50% sodium hydride in mineral oil in 120 mL of tetrahydrofuran. The combination was treated as described in Example 5, Step D, to yield 1.7 grams of 6-phenyl-2-(4,6-dimethoxypyrimidin-2-yloxy)benzoic acid. The nmr spectrum was consistent with the proposed structure.

Workup

  1. customThis compound was prepared in a manner analogous to that of Example 5, Step D
  2. additionThe combination was treated

Sources & evidence

ORD record
ord-aa5836aa2fe74c6f9db057ec2442aeba
Source dataset
uspto-grants-1992_09
Patent number
US05149357

Reaction notes

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