Sodium Iodide → HCID 12004129, compound

HRID 971263Notes

Reaction equation

Cl[C:2]1[C:3]2[CH2:11][CH2:10][N:9]([C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][N:13]=3)[CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[O:19]1[CH2:24][CH2:23][O:22][C:21]2[CH:25]=[C:26]([NH2:29])[CH:27]=[CH:28][C:20]1=2.[I-].[Na+].C(=O)(O)[O-].[Na+]>C(#N)C>[Cl:18][C:17]1[C:12]([N:9]2[CH2:10][CH2:11][C:3]3[C:2]([NH:29][C:26]4[CH:27]=[CH:28][C:20]5[O:19][CH2:24][CH2:23][O:22][C:21]=5[CH:25]=4)=[N:7][CH:6]=[N:5][C:4]=3[CH2:8]2)=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 4-chloro-7-(3-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (0.095 g, 0.00034 mol), 2,3-dihydrobenzo[b][1,4]dioxin-6-amine (0.10 g, 0.00068 mol) and sodium iodide (0.02 g, 0.0001 mol) in acetonitrile was heated at 150° C. by microwave in a sealed tube for 10 minutes. After cooling to r.t., the mixture was poured into saturated sodium bicarbonate and extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate and concentrated to leave an oil. Residue purified by flash chromatography over silica gel (ethyl acetate/hexane gradient 0 to 100%) to give 0.110 g of a white solid.

Workup

temperatureAfter cooling to r.t.
extractionextracted with ethyl acetate
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
concentrationconcentrated
customto leave an oil
customResidue purified by flash chromatography over silica gel (ethyl acetate/hexane gradient 0 to 100%)

Sources & evidence

ORD record: ord-7f2e9f175a32443ea7780458e5a5eba1
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312330B2

Reaction notes

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