Water → HCID 59139351, compound

HRID 2277773Notes

Reaction equation

CS(O)(=O)=O.[F:6][C:7]1[C:8]([NH2:27])=[N:9][CH:10]=[CH:11][C:12]=1[CH2:13][C:14]1[C:15](=[O:26])[O:16][C:17]2[CH:24]=[C:23]([OH:25])[CH:22]=[CH:21][C:18]=2[C:19]=1[CH3:20].Br[C:29]1[N:34]=[CH:33][CH:32]=[CH:31][N:30]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:20][C:19]1[C:18]2[CH:21]=[CH:22][C:23]([O:25][C:29]3[N:34]=[CH:33][CH:32]=[CH:31][N:30]=3)=[CH:24][C:17]=2[O:16][C:15](=[O:26])[C:14]=1[CH2:13][C:12]1[CH:11]=[CH:10][N:9]=[C:8]([NH2:27])[C:7]=1[F:6]

Participants

Conditions

Temperature: 115 °C

Procedure

Under a nitrogen atmosphere, 3-(3-fluoro-2-aminopyridin-4-ylmethyl)-7-hydroxy-4-methyl-2-oxo-2H-1-benzopyran methanesulfonate (7.6 g, 19.2 mmol) and 2-bromopyrimidine (4.0 g, 24.9 mmol) were dissolved in DMF (122 mL), potassium carbonate (5.8 g, 42.2 mmol) was added, and the mixture was stirred at 115° C. for 3.5 hours. The reaction mixture was cooled to 28° C., water (122 mL) was added dropwise over a period of 0.5 hours at that temperature, and the mixture was stirred for 2 minutes. The mixture was further cooled to 0° C. and stirred for 1 hour, and the precipitated crystals were collected by filtration. The obtained crystals were washed with water (61 mL) and acetonitrile (61 mL) in that order, and dried under reduced pressure to obtain the title compound as crystals (6.5 g).

Workup

temperatureThe reaction mixture was cooled to 28° C.
stirringthe mixture was stirred for 2 minutes
temperatureThe mixture was further cooled to 0° C.
stirringstirred for 1 hour
filtrationthe precipitated crystals were collected by filtration
washThe obtained crystals were washed with water (61 mL) and acetonitrile (61 mL) in that order
customdried under reduced pressure

Sources & evidence

ORD record: ord-a0e0a7b9a6944913957d4f9d8ae42dc7
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133174B2

Reaction notes

Loading…