4-t-Butylbenzenesulfonyl chloride → 4-tert-butyl-N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide

HRID 397275Notes

Reaction equation

HRID 397275 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:15][C:16]1[C:21]([O:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])=[C:20]([O:31][CH3:32])[N:19]=[C:18]([C:33]2[N:38]=[CH:37][CH:36]=[CH:35][N:34]=2)[N:17]=1>N1C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:15][C:16]2[C:21]([O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])=[C:20]([O:31][CH3:32])[N:19]=[C:18]([C:33]3[N:38]=[CH:37][CH:36]=[CH:35][N:34]=3)[N:17]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 1398824-t-Butylbenzenesulfonyl chlorideHCID 229997224-Amino-6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-pyrimidine

Product 1

HCID 229997044-tert-butyl-N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamideYield 3.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-tert-Butyl-benzene sulphonyl chloride (286 mg) was added to a stirred solution of 4-amino-6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-pyrimidine (EP 713875A1) (100 mg) in dry pyridine (2 ml) at room temperature and the resulting mixture stirred for 36 hours. The reaction was then partitioned between ethyl acetate (20 ml) and 2N aqueous hydrochloric acid (10 ml) and the organic phase separated, washed (2N aqueous hydrochloric acid 2×10 ml, water 2×10 ml), dried (MgSO4) and evaporated under reduced pressure. Column chromatography on silica eluting with a solvent gradient of pentane:ethyl acetate 25:75 changing to 0:100, then dichloromethane:methanol 95:5 gave 4-tert-butyl-N-[6-methoxy-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]benzenesulfonamide as an off-white coloured solid (5 mg).

Workup

  1. customThe reaction was then partitioned between ethyl acetate (20 ml) and 2N aqueous hydrochloric acid (10 ml)
  2. customthe organic phase separated
  3. washwashed (2N aqueous hydrochloric acid 2×10 ml, water 2×10 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-b9c55d95b4d949b8b8f09fb1262a142b
Source dataset
uspto-grants-2003_08
Patent number
US06610518B2

Reaction notes

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