Ethanol → HCID 178490274, compound

HRID 2110676Notes

Reaction equation

C[N:2](C)[C:3]([CH3:32])=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[CH:18]=[C:17]([NH:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[N:16]=[C:15]([O:30][CH3:31])[N:14]=2)[CH:8]=1)=O.O.[NH2:35]N.CCO.CCOC(C)=O>CCCCCCC>[CH3:31][O:30][C:15]1[N:16]=[C:17]([NH:19][CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)[CH:18]=[C:13]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([C:5]3[NH:35][N:2]=[C:3]([CH3:32])[CH:4]=3)[CH:8]=2)[N:14]=1

Participants

Conditions

Temperature: 85 °C

Procedure

In a sealed tube are combined 3-dimethylamino-1-(3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-phenyl)-but-2-en-1-one [147 mg, 0.33 mmol, Intermediate (47) prepared as described in Example 38, Step 1], hydrazine hydrate (200 μL), and EtOH (3 mL). Heated the mixture to 85° C. and stirred for 1.5 hours. The reaction mixture is concentrated to provide an oil which is subjected to flash column chromatography on silica gel eluting with 20 to 60% EtOAc in heptane gradient, to afford {2-methoxy-6-[3-(5-methyl-2H-pyrazol-3-yl)-phenyl]-pyrimidin-4-yl}-[2-(4-methoxy-phenyl)-ethyl]-amine [136 mg, 99%, Example 39]. LCMS: RT=2.79 minutes, MS: 416 (M+H). 1H NMR (300 MHz, CDCl3), δ 8.29 (1H, s), 7.9 (1H, d, J=0.027 Hz), 7.72 (1H, d, J=0.025 Hz), 7.4 (1H, t, J=0.026 Hz), 7.09 (2H, d, J=0.028 Hz), 6.82 (2H, d, J=0.028 Hz), 6.35 (2H, d, J=0.024 Hz), 5.18 (1H, s), 3.98 (3H, s), 3.75 (3H, s), 3.59 (2H, m), 2.83 (2H, t, J=0.023), 2.3 (3H, s).

Workup

customIn a sealed tube are combined
concentrationThe reaction mixture is concentrated
customto provide an oil which

Sources & evidence

ORD record: ord-dd48cb00d4ab4769840fe89672600344
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07517889B2

Reaction notes

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