Potassium Carbonate → HCID 18402964, compound

HRID 2270898Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A suspension of potassium carbonate (0.36 g), 1-[4-chloro-2-fluoro-5-(2-pyrimidyloxy)phenyl]-1,4-dihydro-5-oxo-5H-tetrazole (0.54 g) and 1-bromo-3-fluoropropane (0.37 g) in N,N-dimethylformamide (10 ml) was stirred in an oil bath at 80° C. for 26 hours. The reaction mixture was processed and the resulting oil chromatographed on silica gel eluting with hexane:ethyl acetate, 2:1, to give the product, mp 111-3° C. 1H NMR (CDCl3, TMS): 2.30(2H, m), 4.20(2H, t, J=6.9 Hz), 4.59(2H, dt, J=46.9, 6.6 Hz), 7.13(1H, dd, J=4.8 Hz), 7.48(1H, d, J=9.3 Hz), 7.58(1H, d, J=6.8 Hz), 8.58(2H, d, J=4.8 Hz).

Workup

customthe resulting oil chromatographed on silica gel eluting with hexane
customethyl acetate, 2:1, to give the product, mp 111-3° C

Sources & evidence

ORD record: ord-a60d605157264a998ede848441e0c325
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06333296B1

Reaction notes

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