Methanesulfonyl chloride → HCID 21846425, compound

HRID 617803Notes

Reaction equation

HRID 617803 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:10]=[C:9]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([F:21])=[CH:13][CH:12]=2)[CH:8]=[C:7]([CH:22]([CH3:24])[CH3:23])[N:6]=1.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>CCOCC>[CH3:25][S:26]([NH:1][CH2:2][CH2:3][NH:4][C:5]1[N:10]=[C:9]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([F:21])=[CH:13][CH:12]=2)[CH:8]=[C:7]([CH:22]([CH3:24])[CH3:23])[N:6]=1)(=[O:28])=[O:27]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 21846229HCID 21846229, compound

Product 1

HCID 21846425HCID 21846425, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 2-(2-aminoethyl)amino-4-(4-fluoronaphth-1-yl)-6-isopropylpyrimidine (0.170 g) dissolved diethyl ether was added dropwise a solution of methansulfonyl chloride (0.060 g) in ether. The reaction was carried out at room temperature, and after 1 hour the solvent was removed under reduced pressure. The crude material was taken up in methylene chloride and the free base was liberated by the addition of sodium carbonate solution. The organic layer was dried over magnesium sulfate and the reaction product isolated by evaporation, purified by column chromatography on silica gel, eluting with ethyl acetate/hexane to give 2-(2-methanesulfonamidoethyl)amino-4-(4-fluoronaphth-1-yl)-6-isopropylpyrimidine. The hydrochloride salt of the product was made (0.180 g), m.p. 85-91° C. (C 54.67%, H 5.59%, N 12.48%).

Workup

  1. customwas carried out at room temperature
  2. customafter 1 hour the solvent was removed under reduced pressure
  3. additionthe free base was liberated by the addition of sodium carbonate solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customthe reaction product isolated by evaporation
  6. custompurified by column chromatography on silica gel
  7. washeluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-3d73e1f270aa4c91a2e0d0616ec53c0a
Source dataset
uspto-grants-1999_09
Patent number
US05952331

Reaction notes

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