1,3-Dibromopropane → HCID 67175933, compound

HRID 1027505Notes

Reaction equation

[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][C:7]2[N:8]=[C:9]([O:25][CH2:26][CH2:27][CH3:28])[C:10]3[N:15]=[C:14]([C:16]4[CH:21]=[C:20]([CH3:22])[C:19]([OH:23])=[C:18]([CH3:24])[CH:17]=4)[O:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[Br:31][CH2:32][CH2:33][CH2:34]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Br:31][CH2:32][CH2:33][CH2:34][O:23][C:19]1[C:18]([CH3:24])=[CH:17][C:16]([C:14]2[O:13][C:11]3[N:12]=[C:7]([CH2:6][C:5]4[CH:29]=[CH:30][C:2]([Cl:1])=[CH:3][CH:4]=4)[N:8]=[C:9]([O:25][CH2:26][CH2:27][CH3:28])[C:10]=3[N:15]=2)=[CH:21][C:20]=1[CH3:22]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 300 mg of 4-[5-(4-chloro-benzyl)-7-propoxy-oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethyl-phenol (example 17), 286 mg of 1,3-dibromopropane and 98 mg of potassium carbonate in 10 ml of dimethylformamide was heated to 60° C. for 3 h. After cooling to room temperature, the solids were removed by filtration. The solvent was distilled off in vacuo and the residue was purified by chromatography (method SC1) to yield 230 mg of the title compound.

Workup

temperatureAfter cooling to room temperature
customthe solids were removed by filtration
distillationThe solvent was distilled off in vacuo
customthe residue was purified by chromatography (method SC1)

Sources & evidence

ORD record: ord-d323898aeadd4dd9962a700218b9bd1f
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735387B2

Reaction notes

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