2,3-Dichloropyridine → 7-(3-Chloropyridin-2-yl)-N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4-amine

HRID 971227Notes

Reaction equation

HRID 971227 reaction equation
C(N(C(C)C)CC)(C)C.[F:10][C:11]([F:32])([F:31])[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[C:20]3[CH2:30][CH2:29][NH:28][CH2:27][C:21]=3[N:22]=[C:23]([S:25][CH3:26])[N:24]=2)=[CH:14][CH:13]=1.Cl[C:34]1[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][N:35]=1>O1CCOCC1.C(N(CC)C(=O)C)C>[Cl:40][C:39]1[C:34]([N:28]2[CH2:29][CH2:30][C:20]3[C:19]([NH:18][C:15]4[CH:16]=[CH:17][C:12]([C:11]([F:31])([F:10])[F:32])=[CH:13][CH:14]=4)=[N:24][C:23]([S:25][CH3:26])=[N:22][C:21]=3[CH2:27]2)=[N:35][CH:36]=[CH:37][CH:38]=1

Participants

6

Reactant 3

HCID 169882,3-DichloropyridineHCID 81531DiisopropylethylamineHCID 59021576N-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4-amine

Product 1

HCID 120043647-(3-Chloropyridin-2-yl)-N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4-amineYield 17%

Reagents, catalysts & solvents 2

HCID 12703N,N-DiethylacetamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
180 °C

Procedure

A mixture of diisopropylethylamine (252 mg, 1.95 mmol), N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4-amine (443 mg, 1.3 mmol) and 2,3-dichloropyridine (386 mg, 2.6 mmol) in dioxane (5 mL) and N,N-diethylacetamide (0.5 mL) was heated via microwave in a sealed tube at 180° C. for 10 h. Solvent was removed in vacuo and residue was purified by column chromatography. The product was obtained as a beige solid (100 mg).

Workup

  1. customSolvent was removed in vacuo and residue
  2. customwas purified by column chromatography

Sources & evidence

ORD record
ord-cb10f7e562d547c0b14b618698064710
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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