Sodium hydride → 3-(3,4-dimethyl-benzoyl)-1-pyrimidin-2-ylmethyl-1H-quinolin-4-one

HRID 226936Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH3:21])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=[O:6].[H-].[Na+].Cl[CH2:25][C:26]1[N:31]=[CH:30][CH:29]=[CH:28][N:27]=1>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH3:21])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:25][C:26]2[N:31]=[CH:30][CH:29]=[CH:28][N:27]=2)[CH:8]=1)=[O:6]

Participants

Conditions

Temperature: 80 °C

Procedure

Compound 4k was prepared following the procedure outlined in Step 3 of Example 1. Briefly described here, 97 mg (0.35 mmol) of 3-(3,4-dimethyl-benzoyl)-1H-quinolin-4-one, 18 mg (0.45 mmol) of 60% sodium hydride and 66 mg (0.51 mmol) of 2-chloromethyl pyrimidine (prepared as described by Paine, J. B.; J. Het. Chem. 1987, 351) were combined in 1 mL N,N-dimethylformamide and heated at 80° C. for 2 h. The product was purified using reverse phase HPLC (mobile phase with a gradient 10-50% acetonitrile in 50 min), to give 57 mg of a pale yellow solid 4k as trifluoroacetate salt: LC-MSD, m/z for C23H19N3O2 [M+H]+=370.5, HPLC retention time: 2.4 min; 1H NMR (400 MHz, CDCl3): δ 2.3 (s, 3H), 2.35 (s, 3H), 5.6 (s, 2H), 7.15-7.2 (m, 1H), 7.25-7.3 (m, 1H), 7.4-7.5 (m, 1H), 7.5-7.55 (m, 1H), 7.6-7.7 (m, 3H), 8.4-8.5 (m, 2H), 8.7-8.75 (m, 2H).

Workup

customCompound 4k was prepared
customThe product was purified
customin 50 min

Sources & evidence

ORD record: ord-71d691c5d9604d988af689a179f345c9
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07557213B2

Reaction notes

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