HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Benzenesulfonamide, 3-amino- → 3-[(4-Chloropyrimidin-2-yl)amino]benzenesulfonamide

HRID 237
Notes
Print preview

Reaction equation

HRID 237 reaction equation
Clc1ccnc(Cl)n1.Nc1cccc(S(N)(=O)=O)c1>C1COCCO1.CC(=O)O.CC(=O)O.CC1(C)c2cccc(P(c3ccccc3)c3ccccc3)c2Oc2c(P(c3ccccc3)c3ccccc3)cccc21.O=C([O-])[O-].[Cs+].[Cs+].[Pd]>NS(=O)(=O)c1cccc(Nc2nccc(Cl)n2)c1
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 7377Benzenesulfonamide, 3-amino-HCID 775312,4-Dichloropyrimidine

Product 1

HCID 889048943-[(4-Chloropyrimidin-2-yl)amino]benzenesulfonamideYield 2%

Reagents, catalysts & solvents 4

HCID 10796Cesium carbonateReagentHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)
Catalyst
HCID 4144353Palladium (II) acetateCatalyst
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

2,4-dichloropyrimidine (200 mg, 1.34 mmol), 3-aminobenzenesulfonamide (231 mg, 1.34 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (93 mg, 0.16 mmol), cesium carbonate (875 mg, 2.68 mmol) and diacetoxypalladium (15.07 mg, 0.07 mmol) were suspended in dioxane (5 mL) and sealed into a microwave tube. The reaction was heated to 150 °C for 30 minutes in the microwave reactor and cooled to RT. The reaction mixture was diluted with EtOAc (150 mL) and washed with water (150 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 4% (10:1 MeOH/NH3 (aq)) in DCM. NMR analysis showed a trace amount of product.

Sources & evidence

ORD record
ord-07751cbdbcad4c89bdfeeea3a04ddb39
Source dataset
750 AstraZeneca ELN dataset
Original link
View source

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureSources & evidenceReaction notes