Methylamine → HCID 66690203, compound

HRID 403533Notes

Reaction equation

HRID 403533 reaction equation
Cl[CH:2]([C:4]1[N:13]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:12](=[O:22])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1)[CH3:3].[CH3:23][NH2:24]>>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([N:13]2[C:12](=[O:22])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]2[CH:2]([NH:24][CH3:23])[CH3:3])=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 6329MethylamineHCID 66689872HCID 66689872, compound

Product 1

HCID 66690203HCID 66690203, compoundYield 99%

Conditions

Temperature
110 °C

Procedure

To the neat 2-(1-chloroethyl)-3-(4-methoxyphenyl)-3H-quinazolin-4-one (1.0 g, 3.2 mmol) in a sealed tube was added 40 mL of a methylamine solution (1M in THF, 40 mmol). The tube was sealed and heated to 110° C. 16 h. The resulting solution was cooled to room temperature and concentrated under vacuum to afford the crude product that was purified by flash chromatography (5% MeOH/DCM, silica gel) to afford the title compound (yield 0.97 g, 99%). 1H-NMR (CD3OD): δ 8.28 (m, 1H), 7.93 (m, 1H), 7.86 (m, 1H), 7.65 (m, 1H), 7.43 (m, 1H) 7.33 (m, 1H), 7.19 (m, 2H), 4.09 (q, 1H), 3.92 (s, 3H), 2.75 (s, 3H), 1.51 (d, 3H).

Workup

  1. customThe tube was sealed
  2. custom16 h
  3. temperatureThe resulting solution was cooled to room temperature
  4. concentrationconcentrated under vacuum
  5. customto afford the crude product that
  6. customwas purified by flash chromatography (5% MeOH/DCM, silica gel)

Sources & evidence

ORD record
ord-742e1bf6f931444cb731ca223d42cac8
Source dataset
uspto-grants-2014_06
Patent number
US08748440B2

Reaction notes

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