Triethylamine → N-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-6-phenylpyrido[4,3-d]pyrimidin-4-amine

HRID 19637

Reaction equation

HRID 19637 reaction equation
[N:1]1[C:6]2[CH2:7][CH2:8][NH:9][CH2:10][C:5]=2[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)=[N:3][CH:2]=1.[C:22]1(B(O)O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(N(CC)CC)C>C1COCC1.CC([O-])=O.CC([O-])=O.[Cu+2]>[F:21][C:18]([F:20])([F:19])[C:15]1[CH:14]=[CH:13][C:12]([NH:11][C:4]2[C:5]3[CH2:10][N:9]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:8][CH2:7][C:6]=3[N:1]=[CH:2][N:3]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 59346476(5,6,7,8-Tetrahydro-pyrido[4,3-d]pyrimidin-4-yl)-(4-trifluoromethylphenyl)amine

Product 1

HCID 59346458N-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-6-phenylpyrido[4,3-d]pyrimidin-4-amineYield 6.4%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The (5,6,7,8-Tetrahydro-pyrido[4,3-d]pyrimidin-4-yl)-(4-trifluoromethylphenyl)amine (100 mg, 0.34 mmol) was dissolved in anhydrous THF (2 mL). To the mixture was added phenylboronic acid (83 mg, 0.68 mmol), Cu(OAc)2 (124 mg, 0.68 mmol) and triethylamine (0.68 g, 0.095 mL). The mixture was agitated for 6 h and the solvent was removed under the vacuum. The residue was purified using a gradient of ethyl acetate:hexane (0-100%) to give the desired compound as reddish powder (8.0 mg, 6.0%).

Workup

  1. customthe solvent was removed under the vacuum
  2. customThe residue was purified

Sources & evidence

ORD record
ord-c5c8838fa6d540bc9becc3ac0dc4c426
Source dataset
uspto-grants-2010_06
Patent number
US07745451B2

Linked notes

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