N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide → 3-(2-aminothieno[3,2-d]pyrimidin-7-yl)-N-methylbenzenesulfonamide

HRID 2042225Notes

Reaction equation

HRID 2042225 reaction equation
Br[C:2]1[C:6]2[N:7]=[C:8]([NH2:11])[N:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[CH3:12][NH:13][S:14]([C:17]1[CH:22]=[CH:21][CH:20]=[C:19](B2OC(C)(C)C(C)(C)O2)[CH:18]=1)(=[O:16])=[O:15]>>[NH2:11][C:8]1[N:9]=[CH:10][C:5]2[S:4][CH:3]=[C:2]([C:21]3[CH:22]=[C:17]([S:14]([NH:13][CH3:12])(=[O:15])=[O:16])[CH:18]=[CH:19][CH:20]=3)[C:6]=2[N:7]=1

Participants

3

Reactant 2

HCID 57416240N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamideHCID 671201377-Bromothieno[3,2-d]pyrimidin-2-amine

Product 1

HCID 671201393-(2-aminothieno[3,2-d]pyrimidin-7-yl)-N-methylbenzenesulfonamideYield 64.6%

Procedure

3-(2-Aminothieno[3,2-d]pyrimidin-7-yl)-N-methylbenzenesulfonamide (180 mg, 64% yield) was prepared in the same manner as Step 6 of Example 1 using 7-bromothieno[3,2-d]pyrimidin-2-amine (200 mg, 0.87 mmol) and N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (260 mg, 0.87 mmol).

Sources & evidence

ORD record
ord-03bc8e297a0e43a989039225faf825a6
Source dataset
uspto-grants-2013_11
Patent number
US08586580B2

Reaction notes

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