4-Chloro-3-methylphenol → 1-Chloro-4-methoxy-2-methylbenzene
Reaction equation
[Cl:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]([OH:8])=[CH:6][CH:7]=1.S(OC)(O[CH3:14])(=O)=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:14])=[CH:4][C:3]=1[CH3:9]Participants
Procedure
4-Chloro-m-cresol was methylated with dimethyl sulfate to give 1-chloro-4-methoxy-2-methylbenzene. This was converted with N -bromosuccinimide into 2-bromomethyl- 1-chloro-4-methoxybenzene. Subsequent alkylation with diethyl malonate yielded diethyl (2-chloro -5-methoxy-benzyl)-malonate. This was condensed with morpholine -formamidine in analogy to Example 1, part d), to give 5-(2-chloro-5-methoxy-benzyl)-2-(morpholin-4-yl)-4,6(1H,5H)-pyrimidinedione. Subsequent chlorination with POCl3 analogously to Example 1e) gave 4,6-dichloro-5-(2-chloro-5-methoxy-benzyl)-2-(morpholin-4-yl)-pyrimidine which was reacted further with (4-tert.butylbenzenesulfonamide) K analogously to Example 1 g) to give 4-tert-butyl-N-[6-chloro-5-(2-chloro -5 -methoxy-benzyl)-2-(morpholin-4-yl)-pyrimidin-4-yl]benzenesulfonamide. Subsequent reaction with sodium ethylene glycolate analogously to Example 1h) finally gave 4-tert-butyl-N-[6-(2-hydroxy-ethoxy)-5-(2-chloro-5-methoxybenzyl)-2-(morpholine-4-yl)pyrimidin-4-yl]-benzenesulfonamide. M.p. 159°-162° C.
Sources & evidence
- ORD record
- ord-a5cd44b82a8448ba9b11ea133330446f
- Source dataset
- uspto-grants-1996_07
- Patent number
- US05541186
Reaction notes
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