5-Tributylstannyl-4-iodo-1-methyl-1H-imidazole → 6-(4-Iodo-1-methyl-1H-imidazol-5-yl)-4-methylthio-thieno[2,3-d]pyrimidine

HRID 32606Notes

Reaction equation

[CH3:1][S:2][C:3]1[C:4]2[CH:11]=[C:10](I)[S:9][C:5]=2[N:6]=[CH:7][N:8]=1.C([Sn](CCCC)(CCCC)[C:18]1[N:22]([CH3:23])[CH:21]=[N:20][C:19]=1[I:24])CCC>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[I:24][C:19]1[N:20]=[CH:21][N:22]([CH3:23])[C:18]=1[C:10]1[S:9][C:5]2[N:6]=[CH:7][N:8]=[C:3]([S:2][CH3:1])[C:4]=2[CH:11]=1

Participants

Conditions

Temperature: 100 °C

Procedure

4-Methylthio-6-iodo-thieno[2,3-d]pyrimidine (Intermediate 91) (949 mg), 5-tributylstannyl-4-iodo-1-methyl-1H-imidazole (Intermediate 92) (2.76 g) and tetrakis(triphenylphosphine)palladium(0) (178 mg) were stirred in anhydrous DMF (50 mL), degassed with nitrogen for 10 min, then heated to 100° C. for 18 hours under an inert atmosphere. The reaction mixture was concentrated in vacuo and the crude product triturated with DCM (20 mL) to afford the title compound as a yellow solid (805 mg, 67%);

Workup

customdegassed with nitrogen for 10 min
concentrationThe reaction mixture was concentrated in vacuo
customthe crude product triturated with DCM (20 mL)

Sources & evidence

ORD record: ord-30357bc705ba40d99b2de1f23d4a355d
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07427616B2

Reaction notes

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