2,3-Dichloropyridine → N-(4-tert-Butylphenyl)-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4-amine

HRID 2219960Notes

Reaction equation

HRID 2219960 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[C:22]3[CH2:32][CH2:31][NH:30][CH2:29][C:23]=3[N:24]=[C:25]([S:27][CH3:28])[N:26]=2)=[CH:16][CH:15]=1)([CH3:13])([CH3:12])[CH3:11].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>[C:10]([C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]2[C:22]3[CH2:32][CH2:31][N:30]([C:34]4[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][N:35]=4)[CH2:29][C:23]=3[N:24]=[C:25]([S:27][CH3:28])[N:26]=2)=[CH:16][CH:15]=1)([CH3:13])([CH3:11])[CH3:12]

Participants

6

Reactant 3

HCID 169882,3-DichloropyridineHCID 81531DiisopropylethylamineHCID 59021569N-(4-tert-Butylphenyl)-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4-amine

Product 1

HCID 12004390N-(4-tert-Butylphenyl)-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4-amineYield 25%

Reagents, catalysts & solvents 2

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

Procedure

The solution of diisopropylethylamine (235 mg, 1.82 mmol), N-(4-tert-butylphenyl)-5,6,7,8-tetrahydro-2-(methylthio)pyrido[3,4-d]pyrimidin-4-amine (300 mg, 0.91 mmol) and 2,3-dichloropyridine (270 mg, 1.82 mmol) in dioxane (5 mL) and N,N-diethylacetamide (0.5 mL) was irradiated in microwave at 180° C. for 10 hr. Solvent was removed in vacuo and residue was dissolved in ethyl acetate, washed by water, brine, dried over sodium sulfate and purified by column chromatography, product was obtained as a beige solid (100 mg, 25%).

Workup

  1. customSolvent was removed in vacuo and residue
  2. dissolutionwas dissolved in ethyl acetate
  3. washwashed by water, brine
  4. dry with materialdried over sodium sulfate
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-87cea556d53f4d84b46862ec69ab35d4
Source dataset
uspto-grants-2008_08
Patent number
US07414131B2

Reaction notes

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