2-(4-Benzyloxycarbonyl-2-methoxy-phenylamino)-4-chloro-5-trifluoromethyl-pyrimidine → 2-(4-Carboxy-2-methoxy-phenylamino)-4-chloro-5-trifluoromethyl-pyrimidine

HRID 388360Notes

Reaction equation

HRID 388360 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:28]=[CH:27][C:16]([C:17]([O:19]CC3C=CC=CC=3)=[O:18])=[CH:15][C:14]=2[O:29][CH3:30])[N:3]=1>C1COCC1.[OH-].[OH-].[Pd+2]>[Cl:1][C:2]1[C:7]([C:8]([F:10])([F:9])[F:11])=[CH:6][N:5]=[C:4]([NH:12][C:13]2[CH:28]=[CH:27][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=2[O:29][CH3:30])[N:3]=1

Participants

4

Reactant 1

HCID 582010032-(4-Benzyloxycarbonyl-2-methoxy-phenylamino)-4-chloro-5-trifluoromethyl-pyrimidine

Product 1

HCID 589063992-(4-Carboxy-2-methoxy-phenylamino)-4-chloro-5-trifluoromethyl-pyrimidine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Benzyl 4-(4-chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-3-methoxy-benzoate (A3-a) (1.3 g, 3 mmol) is suspended in a hydrogenating autoclave in 50 mL THF and mixed with Pd(OH)2 on charcoal (180 mg, charge 20%, approx. 50% water). Then 4.5 bar H2 pressure are applied and the reaction mixture is stirred for 24 h. After the reaction has ended the reaction mixture is filtered, the filtrate is evaporated down and the crude product A-4a (HPLC-MS: tRet.=1.24 min; MS (M−H)+=346) is used in the subsequent reactions without any further purification.

Workup

  1. filtrationis filtered
  2. customthe filtrate is evaporated down
  3. customthe crude product A-4a (HPLC-MS: tRet.=1.24 min; MS (M−H)+=346) is used in the subsequent reactions without any further purification

Sources & evidence

ORD record
ord-d36a0358c14646519c09fb502ebc7aba
Source dataset
uspto-grants-2013_02
Patent number
US08377943B2

Reaction notes

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