Water → N-[3-(2-chloro-5-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl)phenyl]methanesulfonamide

HRID 1615593Notes

Reaction equation

[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:10]([CH3:11])[CH:9]=[C:8](I)[C:6]=2[N:7]=1.[CH3:13][S:14]([NH:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][CH:23]=1)(=[O:16])=[O:15].C([O-])([O-])=O.[Na+].[Na+].O>CN(C=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[N:10]([CH3:11])[CH:9]=[C:8]([C:22]3[CH:23]=[C:18]([NH:17][S:14]([CH3:13])(=[O:15])=[O:16])[CH:19]=[CH:20][CH:21]=3)[C:6]=2[N:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-chloro-7-iodo-5-methyl-5H-pyrrolo[3,2-d]pyrimidine (0.140 g, 0.48 mmol, 1.0 eq.) in DMF (6 ml) was added 3-methanesulfonylaminophenylboronic acid (0.124 g, 0.576 mmol, 1.2 eq.) followed by aqueous Na2CO3 (2M, 0.7 ml, 1.44 mmol, 3.0 eq.). A flow of nitrogen was bubbled through the mixture during 15 to 20 min before adding Pd[PPh3]4 (0.055 g, 0.048 mmol, 0.1 eq.). The mixture was then heated up to 100° C. overnight. After cooling down the reaction mixture to room temperature a large amount of water (around 60 ml) was added and the mixture extracted with ethyl acetate (3 times). After evaporation the residue was purified by column chromatography using petroleum spirit/ethyl acetate (1:4) as eluent. The product was obtained as a pale yellow solid (110 mg, 68%). LRMS (EI): m/z calcd for [M+H]+ 337.05 found 337.2.

Workup

customA flow of nitrogen was bubbled through the mixture during 15 to 20 min
additionwas added
extractionthe mixture extracted with ethyl acetate (3 times)
customAfter evaporation the residue
customwas purified by column chromatography

Sources & evidence

ORD record: ord-68865f6e2ae54de794616a32f7663cb1
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08765755B2

Reaction notes

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