Triethylamine → HCID 59490408, compound

HRID 2383410Notes

Reaction equation

HRID 2383410 reaction equation
[CH3:1][NH:2][C:3]1[N:12]=[CH:11][C:10]2[C:9](=[O:13])[CH2:8][CH2:7][CH2:6][C:5]=2[N:4]=1.CO[CH:16](OC)[N:17]([CH3:19])[CH3:18].C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:16][N:17](/[CH:19]=[C:8]1/[C:9](=[O:13])[C:10]2[CH:11]=[N:12][C:3]([NH:2][CH3:1])=[N:4][C:5]=2[CH2:6][CH2:7]/1)[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 78373Dimethylformamide dimethyl acetalHCID 59490507HCID 59490507, compound

Product 1

HCID 59490408HCID 59490408, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-(methylamino)-7,8-dihydroquinazolin-5(6H)-one (0.2 g, 1 mmol) in toluene (3 mL) was added 1,1-dimethoxy-N,N-dimethylmethanamine (0.35 mL, 2.9 mmol) and triethylamine (0.15 mL, 1 mmol). The reaction mixture was refluxed for 16 hours. The reaction mixture was then concentrated under reduced pressure. The crude product was purified by flash column chromatography (SiO2, gradient from 100% chloroform to 2% methanol in chloroform) to give the desired product (0.1 g, 38%) as solid. 1H NMR (CDCl3, 400 MHz): δ 8.84 (bs, 1H), 7.62 (s, 1H), 5.68 (bs, 1H), 3.15 (s, 6H), 3.12 (d, J=6.0 Hz, 3H), 3.10-3.05 (m, 2H), 3.03-2.98 (m, 2H). LCMS [M+H]: 233.

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hours
  2. concentrationThe reaction mixture was then concentrated under reduced pressure
  3. customThe crude product was purified by flash column chromatography (SiO2, gradient from 100% chloroform to 2% methanol in chloroform)

Sources & evidence

ORD record
ord-4a746f3e3be74996a5f89c89240d5749
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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