Sodium Iodide → N-(4-(difluoromethoxy)phenyl)-7-(3-(trifluoromethyl)pyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine

HRID 971267Notes

Reaction equation

Cl[C:2]1[C:3]2[CH2:11][CH2:10][N:9]([C:12]3[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][N:13]=3)[CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[F:22][C:23](F)([F:32])[O:24][C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1.C(#N)C.[I-].[Na+]>C(OCC)(=O)C>[F:22][CH:23]([F:32])[O:24][C:25]1[CH:26]=[CH:27][C:28]([NH:29][C:2]2[C:3]3[CH2:11][CH2:10][N:9]([C:12]4[C:17]([C:18]([F:21])([F:20])[F:19])=[CH:16][CH:15]=[CH:14][N:13]=4)[CH2:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:30][CH:31]=1

Participants

Conditions

Temperature: 150 °C

Procedure

In a 5 mL microwave vial was combined 4-chloro-7-(3-(trifluoromethyl)pyridin-2-yl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine (0.113 g, 0.000356 mol), 4-(trifluoromethoxy)aniline (0.0964 mL, 0.000711 mol), acetonitrile (2 mL, 0.04 mol), and sodium iodide (0.00533 g, 0.0000356 mol). The mixture was heated at at 150° C. for 10 minutes and reduced in vacuo. The remaining solid was taken up in ethyl acetate (10 mL) and washed with saturated sodium bicarbonate (2×10 mL) and water (1×10 mL). The organic layer was dried over magnesium sulfate and reduced in vacuo to yield an off white solid. The mixture was purified by flash chromatography using an ethyl acetate:hexanes (0-50%) gradient to yield the desired product as an off white solid (0.052 g).

Workup

washwashed with saturated sodium bicarbonate (2×10 mL) and water (1×10 mL)
dry with materialThe organic layer was dried over magnesium sulfate
customto yield an off white solid
customThe mixture was purified by flash chromatography

Sources & evidence

ORD record: ord-255d22f923ba4c4184747a58601e3f4a
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312330B2

Reaction notes

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