Ammonia → 5-(Pyridin-3-yl)-3-(pyrimidin-5-yl)isoxazole

HRID 390476Notes

Reaction equation

HRID 390476 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:5]=[N:6][CH:7]=[N:8][CH:9]=1.[C:11]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)#[CH:12].N>>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:11]2[O:1][N:2]=[C:3]([C:4]3[CH:5]=[N:6][CH:7]=[N:8][CH:9]=3)[CH:12]=2)[CH:14]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 1860033-EthynylpyridineHCID 86636847N-Hydroxypyrimidine-5-carbimidoyl chloride

Product 1

HCID 690001035-(Pyridin-3-yl)-3-(pyrimidin-5-yl)isoxazole

Procedure

The titled compound was prepared as the bishydrochloride salt according to Method CB using the product of Example 44B (79 mg, 0.5 mmol) and 3-ethynylpyridine (Aldrich, 52 mg, 0.5 mmol). 1H NMR (300 MHz, DMSO-d6) δ 7.70 (ddd, J=8.1, 4.9, 0.8 Hz, 1H), 7.96 (s, 1H), 8.37 (ddd, J=8.2, 1.9, 1.7 Hz, 1H), 8.77 (dd, J=4.7, 1.7 Hz, 1H), 9.17 (dd, J=2.2, 0.8 Hz, 1H), 9.34 (s, 2H), 9.36 (s, 1H) ppm; MS (DCI/NH3) m/z 225 (M+H)+.

Sources & evidence

ORD record
ord-82b3bb5ac76e4662a26d831cfae6d628
Source dataset
uspto-grants-2013_02
Patent number
US08383658B2

Reaction notes

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