Methyl 3-boronobenzenesulfonamide → 3-(4-amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)-N-methylbenzenesulfonamide

HRID 1485495Notes

Reaction equation

HRID 1485495 reaction equation
Br[C:2]1[C:6]2[N:7]=[C:8]([Cl:12])[N:9]=[C:10]([NH2:11])[C:5]=2[S:4][CH:3]=1.[CH3:13][NH:14][S:15]([C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1)(=[O:17])=[O:16]>>[NH2:11][C:10]1[C:5]2[S:4][CH:3]=[C:2]([C:20]3[CH:19]=[C:18]([S:15]([NH:14][CH3:13])(=[O:16])=[O:17])[CH:23]=[CH:22][CH:21]=3)[C:6]=2[N:7]=[C:8]([Cl:12])[N:9]=1

Participants

3

Reactant 2

HCID 44886921Methyl 3-boronobenzenesulfonamideHCID 866756507-Bromo-2-chlorothieno[3,2-d]pyrimidin-4-amine

Product 1

HCID 866756543-(4-amino-2-chlorothieno[3,2-d]pyrimidin-7-yl)-N-methylbenzenesulfonamideYield 71.2%

Procedure

The target compound (480 mg, 71% yield) was prepared in the same manner as Step 1 of Example 11 using 7-bromo-2-chlorothieno[3,2-d]pyrimidin-4-amine (500 mg, 1.90 mmol) and 3-(N-methylsulfamoyl)phenylboronic acid (409 mg, 1.90 mmol).

Sources & evidence

ORD record
ord-c5aa2db9f31e42d9b0334b1599b23794
Source dataset
uspto-grants-2016_08
Patent number
US09422307B2

Reaction notes

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