Water → [7-(3-Methanesulfonyl-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yl]-(4-trifluoromethyl-phenyl)-amine

HRID 971200Notes

Reaction equation

HRID 971200 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[C:11]3[CH2:19][CH2:18][NH:17][CH2:16][C:12]=3[N:13]=[CH:14][N:15]=2)=[CH:5][CH:4]=1.Cl[C:23]1[C:28]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:27][CH:26]=[CH:25][N:24]=1.C(N(CC)C(C)C)(C)C.O>O1CCOCC1.CN(C)C(=O)C>[CH3:32][S:29]([C:28]1[C:23]([N:17]2[CH2:18][CH2:19][C:11]3[C:10]([NH:9][C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:20])[F:21])=[CH:8][CH:7]=4)=[N:15][CH:14]=[N:13][C:12]=3[CH2:16]2)=[N:24][CH:25]=[CH:26][CH:27]=1)(=[O:31])=[O:30]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 125137462-Chloro-3-(methanesulfonyl)pyridineHCID 59021462(5,6,7,8-Tetrahydro-pyrido[3,4-d]pyrimidin-4-yl)-(4-trifluoromethylphenyl)amine

Product 1

HCID 12004321[7-(3-Methanesulfonyl-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[3,4-d]pyrimidin-4-yl]-(4-trifluoromethyl-phenyl)-amineYield 49.1%

Reagents, catalysts & solvents 1

HCID 67000103dioxane N,N-dimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

N-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine (0.100 g, 0.34 mmol) was dissolved in a mixture of dioxane/N,N-dimethylacetamide (10:1) (1.1 mL). To the solution was added 2-chloro-3-(methylsulfonyl)pyridine (Ponticello et al, J. Org. Chem., 44(17), 1979) (0.128 mg, 0.67 mmol) and N,N-diisopropylethylamine (0.09 mL, 0.51 mmol). The mixture was heated via microwave (Emrys Optimizer model, Personal Chemistry) at 150° C. for 20 min. The reaction mixture was poured into water (20 mL) and extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated to leave a solid. The solid was purified by silica gel chromatography using a gradient of ethyl acetate:hexane (0-100%) to give the desired compound as an white solid (75 mg).

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto leave a solid
  6. customThe solid was purified by silica gel chromatography

Sources & evidence

ORD record
ord-1ab1559fa4ff4322a9fdab673f556899
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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