Methyl iodide → HCID 58574139, compound

HRID 1619349Notes

Reaction equation

HRID 1619349 reaction equation
[CH3:1][C:2]1([CH3:25])[CH2:15][N:14]2[C:5](=[N:6][C:7]3[C:12]([C:13]2=[O:16])=[CH:11][CH:10]=[C:9]([C:17]#[C:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=2)[CH:8]=3)[NH:4][CH2:3]1.[H-].[Na+].[CH3:28]I>C1COCC1>[CH3:28][N:4]1[C:5]2=[N:6][C:7]3[C:12]([C:13](=[O:16])[N:14]2[CH2:15][C:2]([CH3:25])([CH3:1])[CH2:3]1)=[CH:11][CH:10]=[C:9]([C:17]#[C:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[CH:8]=3

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136196111HCID 136196111, compound

Product 1

HCID 58574139HCID 58574139, compoundYield 9.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3,3-dimethyl-9-(pyridin-2-ylethynyl)-3,4-dihydro-1H-pyrimido[2,1-b]quinazolin-6(2H)-one (30 mg, 0.09 mmol), NaH (14 mg, 0.36 mmol) and MeI (28 mg, 0.2 mmol) in dry THF was stirred for 24 h at room temperature. Then the solvent was evaporated to give the crude product, which was purified by column chromatography to give 3 mg of the title compound. MS (ESI): 345 (MH+). 1H NMR (300 MHz, CDCl3) δ 8.66-8.65 (d, J=4.8 Hz, 1H), 8.08-8.05 (d, J=8.2 Hz, 1H), 7.75-7.69 (td, J=7.8, 1.8 Hz, 1H), 7.60-7.55 (m, 2H), 7.31-7.30 (m, 2H), 3.82 (s, 2H), 3.28 (s, 3H), 3.18 (s, 2H), 1.13 (s, 6H).

Workup

  1. customThen the solvent was evaporated
  2. customto give the crude product, which
  3. customwas purified by column chromatography

Sources & evidence

ORD record
ord-956f9b947ab148f381780f55c9833eb5
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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