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 971234Notes

Reaction equation

HRID 971234 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 with water and brine and dried over sodium sulfate and purified by column chromatography, product was obtained as a beige solid (100 mg).

Workup

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

Sources & evidence

ORD record
ord-3928d8c3788b4a6a912474ed892cb684
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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