Water → 3-[3-(5-bromopyrimidin-2-yl)benzyl]-5-trifluoromethyl-3H-benzothiazol-2-one

HRID 330805Notes

Reaction equation

[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[CH:5][C:6]2[S:10][C:9](=[O:11])[NH:8][C:7]=2[CH:12]=1.[Br:15][C:16]1[CH:17]=[N:18][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28]Cl)[CH:23]=2)=[N:20][CH:21]=1.O>CN(C=O)C>[Br:15][C:16]1[CH:21]=[N:20][C:19]([C:22]2[CH:23]=[C:24]([CH:25]=[CH:26][CH:27]=2)[CH2:28][N:8]2[C:7]3[CH:12]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=[CH:5][C:6]=3[S:10][C:9]2=[O:11])=[N:18][CH:17]=1

Participants

Conditions

Temperature: 80 °C

Procedure

1 g (4.56 mmol) of 5-trifluoromethyl-3H-benzothiazol-2-one, 1.3 g (4.56 mmol) of 5-bromo-2-(3-chloromethylphenyl)pyrimidine and 4.5 g (13.69 mmol) of caesium carbonates are suspended in 15 ml of DMF and stirred at room temperature for 15 h and at 80° C. for 3 h. The suspension is added to water, and the precipitate is filtered off with suction, washed with methanol and dried in vacuo, giving beige crystals; HPLC: Rt.=3.72 min (method A);

Workup

filtrationthe precipitate is filtered off with suction
washwashed with methanol
customdried in vacuo
customgiving beige crystals
custom=3.72 min (method A)

Sources & evidence

ORD record: ord-91deb8c4503a40b5a81d26a5843a5c7f
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877751B2

Reaction notes

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