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

HRID 1698087Notes

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, 2H) 7.91 (d, 1H) 7.35 (d, 1H) 7.10 (dd, 1H) 5.53 (br s, 1H) 3.90 (s, 3H) 3.11 (d, 3H); 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-17ffe27f25474d3ea1bc6d5e030b7c37
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163928B2

Reaction notes

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