Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([O:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]3[C:21]=2[C:19](=[O:20])[O:18][CH:17]3O)[N:4]=1.[C-:23]#[N:24].[K+].Cl.[OH2:27]>>[C:23]([CH:17]1[C:16]2[C:21](=[C:12]([O:11][C:5]3[N:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[N:6]=3)[CH:13]=[CH:14][CH:15]=2)[C:19](=[O:20])[O:18]1)(=[O:27])[NH2:24]Participants
5
Procedure
1.0 g of 7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-3-hydroxy-phthalide (see Example 84) is introduced into a solution of 2.1 g of potassium cyanide in 15 ml of water and the whole is treated dropwise at from -7° to -3° C., with cooling, over a period of 10 minutes, with 10 ml of concentrated hydrochloric acid. It is subsequently stirred at room temperature for approximately 16 hours and the crystals which have separated are then filtered off. They are washed with water and recrystallised from acetone/n-hexane to yield 0.2 g of 3-carbamoyl-7-[(4,6-dimethoxy-pyrimidin-2-yl)oxy]-phthalide (see also Example 17).
Workup
- additionthe whole is treated dropwise at from -7° to -3° C.
- customthe crystals which have separated
- filtrationare then filtered off
- washThey are washed with water
- customrecrystallised from acetone/n-hexane
Sources & evidence
- ORD record
- ord-5db9dc541d104704a857d69cebb76a01
- Source dataset
- uspto-grants-1995_06
- Patent number
- US05428002
Linked notes
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