Ethyl Acetate → 5-(5-methoxy-1,3-benzothiazol-2-yl)-N-methylpyridin-2-amine

HRID 1851768Notes

Reaction equation

CO[C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][S:9][C:5]=2[CH:4]=1.Br[C:13]1[CH:14]=N[C:16]([NH:19][CH3:20])=[N:17][CH:18]=1.[CH3:21][O:22]C1N=CC(C2SC3C=CC=CC=3N=2)=CN=1.[CH3:38]COC(C)=O>O>[CH3:21][O:22][C:11]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([C:13]3[CH:14]=[CH:38][C:16]([NH:19][CH3:20])=[N:17][CH:18]=3)=[N:7][C:6]=2[CH:10]=1

Participants

Conditions

Temperature: 170 °C

Procedure

6-Methoxy-1,3-benzothiazole (0.100 g, 0.61 mmol) and 5-bromo-N-methylpyrimidin-2-amine (0.171 g, 0.91 mmol) were reacted according to the procedure used for the preparation of 2-(2-methoxypyrimidin-5-yl)-1,3-benzothiazole with the exception that the reaction was heated at 170° C. in a microwave reactor for 1.5 h. The reaction mixture was diluted with EtOAc and water and the mixture was filtered. The phases were separated and the aqueous layer was extracted with EtOAc (3×). The organic phase was washed with brine (2×), dried (MgSO4) and concentrated under vacuum. Flash chromatography (Heptane/EtOAc gradient) gave the title compound (54 mg) as a yellow solid. 1H NMR (CHLOROFORM-d) δ 8.93 (s, 2 H) 7.91 (d, 1 H) 7.35 (d, 1 H) 7.10 (dd, 1 H) 5.53 (br s, 1 H) 3.90 (s, 3 H) 3.11 (d, 3 H); MS m/z (M+H) 273.

Workup

filtrationthe mixture was filtered
customThe phases were separated
extractionthe aqueous layer was extracted with EtOAc (3×)
washThe organic phase was washed with brine (2×)
dry with materialdried (MgSO4)
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-a7b0326a1dcd4c71a31b0a0c124b066f
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957215B2

Reaction notes

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