Reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:17]=[CH:16][C:15]2[O:14][C:13]3[C:8](=[CH:9][C:10]([C:18]4[CH:19]=[N:20][CH:21]=[N:22][CH:23]=4)=[CH:11][CH:12]=3)[C:7]([CH:25]=[CH2:26])(O)[C:6]=2[CH:5]=1.[NH2:27][C:28]([NH2:30])=[S:29]>CC(O)=O>[CH3:2][O:3][C:4]1[CH:17]=[CH:16][C:15]2[O:14][C:13]3[C:8](=[CH:9][C:10]([C:18]4[CH:23]=[N:22][CH:21]=[N:20][CH:19]=4)=[CH:11][CH:12]=3)[C:7]3([CH2:25][CH2:26][S:29][C:28]([NH2:30])=[N:27]3)[C:6]=2[CH:5]=1Participants
5
Procedure
2 N HCl (3 mL) was added to solution of 2-methoxy-7-(pyrimidin-5-yl)-9-vinyl-9H-xanthen-9-ol (50 mg, 0.150 mmol) and thiourea (9.25 pt, 0.171 mmol) in HOAc (5 mL). The reaction mixture was allowed to stir overnight at rt and concentrated under reduced pressure. The residue was treated with of TFA (4 mL). The reaction mixture was stirred overnight at rt. The reaction mixture was concentrated under reduced pressure and the residue was treated with aqueous, half-saturated sodium bicarbonate, extracted with EtOAc, and concentrated under reduced pressure. The residue was purified by chromatography (DCM/MeOH 20:1 to 5:1) to give 2′-methoxy-7′-(pyrimidin-5-yl)-5,6-dihydrospiro[[1,3]thiazine-4,9′-xanthen]-2-amine as an off-white solid.
Workup
- concentrationconcentrated under reduced pressure
- additionThe residue was treated with of TFA (4 mL)
- stirringThe reaction mixture was stirred overnight at rt
- concentrationThe reaction mixture was concentrated under reduced pressure
- additionthe residue was treated with aqueous, half-saturated sodium bicarbonate
- extractionextracted with EtOAc
- concentrationconcentrated under reduced pressure
- customThe residue was purified by chromatography (DCM/MeOH 20:1 to 5:1)
Sources & evidence
- ORD record
- ord-48def30437704d0ebf43ff7490b9beda
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08497264B2
Linked notes
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