Pyridine → HCID 73950561, compound

HRID 660000Notes

Reaction equation

HRID 660000 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[CH:22]=[C:21]([Cl:23])[N:20]=[CH:19][N:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.N1C=CC=CC=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl>[Cl:23][C:21]1[N:20]=[CH:19][N:18]=[C:17]([NH:16][C:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[C:2]([NH:1][S:31]([CH3:30])(=[O:33])=[O:32])[CH:3]=2)[CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 86038807HCID 86038807, compound

Product 1

HCID 73950561HCID 73950561, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(3′-amino-4′benzyloxyphenyl)amino-6-chloro-pyrimidine (630 mg) in dry dichloromethane was added pyridine (8 ml) followed by methane sulfonyl chloride (0.3 ml). The mixture was stirred at room temperature overnight then evaporated under reduced pressure. The residue was dissolved in water and dichloromethane and the organic phase separated, washed with water, dried (MgSO4) and evaporated under reduced pressure. The residue was then subjected to column chromatography (SiO2;ethyl acetate:petroleum ether (40/60) 1:1) to afford N-{5-[6-chloropyrimidin-4-ylamino]-2-benzyloxy-phenyl}-methanesulfonamide (200 mg). δH (d6 DMSO): 3.14 (3H, s, SO2Me), 5.40 (2H, s, CH2Ph), 6.94 (1H, s, HetH), 7.30-7.40 (1H, m, ArH), 7.50-7.85 (7H, m, ArH), 8.70 (1H, s, HetH), 9.30 (1H, s, NH), 10.00 (1H, s, NH)

Workup

  1. customthen evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in water
  3. customdichloromethane and the organic phase separated
  4. washwashed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-720421c5cb3d4856b40cd7d94ff8e5be
Source dataset
uspto-grants-2011_12
Patent number
US08084457B2

Reaction notes

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