Toluene → HCID 137329726, compound

HRID 1689934Notes

Reaction equation

Br[C:2]1[C:3]2[S:25][CH:24]=[CH:23][C:4]=2[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][SiH2:15][C:16]([CH3:22])([CH3:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH:9]=2)[N:7]=1.CC1(C)C(C)(C)OB([C:34]2[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>C(Cl)(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.C(O)C>[N:37]1[CH:38]=[CH:39][C:34]([C:2]2[C:3]3[S:25][CH:24]=[CH:23][C:4]=3[N:5]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([O:14][SiH2:15][C:16]([CH3:22])([CH3:21])[C:17]([CH3:20])([CH3:19])[CH3:18])[CH:9]=3)[N:7]=2)=[CH:35][CH:36]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 4-bromo-2-[3-(1,1,2,2-tetramethyl-propylsilanyloxy)-phenyl]-thieno[3,2-d]pyrimidine, (72 mg), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-pyridine (52 mg), sodium carbonate (57 mg), PdCl2(PPh3)2 (0.1 eq), toluene (2 mL), ethanol (1 mL) and water (0.5 mL) was heated to 130° C. for 5 minutes under microwave irradiation. The reaction mixture was cooled, diluted with chloroform, washed with brine, dried (MgSO4) and the solvent was removed in vacuo. The residue was purified using flash chromatography to yield 4-pyridin-4-yl-2-[3-(1,1,2,2-tetramethyl-propylsilanyloxy)-phenyl]-thieno[3,2-d]pyrimidine (67 mg).

Workup

temperatureThe reaction mixture was cooled
washwashed with brine
dry with materialdried (MgSO4)
customthe solvent was removed in vacuo
customThe residue was purified

Sources & evidence

ORD record: ord-be4f0b5e15ea4fe883828373ca328916
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153639B2

Reaction notes

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