Bromobenzene → 7-(Phenyl)-N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine

HRID 971242Notes

Reaction equation

C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.Br[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[F:60][C:61]([F:80])([F:79])[C:62]1[CH:67]=[CH:66][C:65]([NH:68][C:69]2[C:70]3[CH2:78][CH2:77][NH:76][CH2:75][C:71]=3[N:72]=[CH:73][N:74]=2)=[CH:64][CH:63]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[C:48]1([N:76]2[CH2:77][CH2:78][C:70]3[C:69]([NH:68][C:65]4[CH:64]=[CH:63][C:62]([C:61]([F:80])([F:60])[F:79])=[CH:67][CH:66]=4)=[N:74][CH:73]=[N:72][C:71]=3[CH2:75]2)[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

Participants

Conditions

Temperature: 160 °C

Procedure

To 2 mL of Dioxane was added 10 mol % of palladium(II)acetate (12 mg) and 20 mol % rac-BINAP (58 mg). After stirring for 3 hours, bromobenzene was added (0.054 ml, 0.53 mmol), cesium carbonate (682 mg, 2.12 mmol), N-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine (150 mg, 0.51 mmol) and activated molecular sieves (340 mg). The mixture was sonicated for 10 minutes and heated in a sealed tube via microwave at 160° C. for 3 hours in a Personal Chemistry Microwave (Smith Creator). After completion, the mixture was filtered through celite, evaporated and purified by flash chromatography over silica gel using a 0-100% gradient of ethyl acetate/hexanes to give the desired product as a white solid (36 mg).

Workup

customThe mixture was sonicated for 10 minutes
filtrationAfter completion, the mixture was filtered through celite
customevaporated
custompurified by flash chromatography over silica gel using a 0-100% gradient of ethyl acetate/hexanes

Sources & evidence

ORD record: ord-ad5002f7df4d43ef8a78bfd078373209
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312330B2

Reaction notes

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