Dimethylamine → HCID 178487757, compound

HRID 241035Notes

Reaction equation

HRID 241035 reaction equation
[CH3:1][NH:2][CH3:3].Cl.Cl[CH2:6][C:7]1[N:16]=[C:15]([OH:17])[C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[CH:12][CH:13]=2)[N:8]=1>>[CH3:1][N:2]([CH2:6][C:7]1[N:16]=[C:15]([OH:17])[C:14]2[C:9](=[CH:10][C:11]([O:18][CH3:19])=[CH:12][CH:13]=2)[N:8]=1)[CH3:3]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 178487747HCID 178487747, compound

Product 1

HCID 178487757HCID 178487757, compoundYield 97.6%

Conditions

Temperature
50 °C

Procedure

To a solution of dimethylamine (2M solution in tetrahydrofuran, 40.0 mL, 80.0 mmol) was added 2-(chloromethyl)-7-(methyloxy)quinazolin-4-ol hydrochloride (7.5 g, 29 mmol) and the reaction mixture was stirred for 90 minutes at 50° C. After cooling it to room temperature the reaction mixture was concentrated and the residue was partitioned between water (100 mL) and ethyl acetate (250 mL). The organic layer was separated and washed with water (100 mL), saturated sodium bicarbonate (100 mL) and brine (100 mL), dried over sodium sulfate, filtered and concentrated to give 2-[(dimethylamino)methyl]-7-(methyloxy)quinazolin-4-ol (6.6 g, 97%). MS (EI) for C12H15N3O2: 234 (MH+).

Workup

  1. temperatureAfter cooling it to room temperature the reaction mixture
  2. concentrationwas concentrated
  3. customthe residue was partitioned between water (100 mL) and ethyl acetate (250 mL)
  4. customThe organic layer was separated
  5. washwashed with water (100 mL), saturated sodium bicarbonate (100 mL) and brine (100 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b4cb3f57005e4f08a7cd19e0fe3f6e52
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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