Formaldehyde → (4-Dimethylamino-phenyl)-(2-methyl-quinazolin-4-yl)-methyl-amine

HRID 1876126Notes

Reaction equation

HRID 1876126 reaction equation
[CH3:1][C:2]1[N:11]=[C:10]([N:12]([C:14]2[CH:19]=[CH:18][C:17](N)=[CH:16][CH:15]=2)[CH3:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[CH2:21]=O.[C:23]([BH3-])#[N:24].[Na+]>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O>[CH3:21][N:24]([CH3:23])[C:17]1[CH:18]=[CH:19][C:14]([N:12]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([CH3:1])[N:11]=2)[CH3:13])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 11311597N-methyl-N-(2-methylquinazolin-4-yl)benzene-1,4-diamine

Product 1

HCID 11403596(4-Dimethylamino-phenyl)-(2-methyl-quinazolin-4-yl)-methyl-amineYield 80%

Reagents, catalysts & solvents 1

HCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

Procedure

To a solution of (2-methyl-quinazolin-4-yl)-(4-amino-phenyl)-methylamine (14 mg, mmol) in 1.5 mL of 37% aqoues formaldehyde solution and 10 uL of glacial acetic was added Sodium cyanoborohydride (15 mg, 0.24 mmol) and the mixture was stirred at room temperature for 2 h. The reaction mixture was quenched by adding 50 uL of 1N HCl. It was diluted with 50 mL of ethyl acetate, washed with saturated sodium bicarbonate, and followed by saturated sodium chloride. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The residue was purified by column chromatography (25% ethyl acetate/hexanes) on silica gel to give the title compound (12.4 mg, 0.042 mmol, 80%). 1H NMR (CDCl3): 7.71 (m, 1H), 7.50 (ddd, J=8.4, 6.9, 1.5, 1H), 7.03-7.09 (m, 3H), 6.95 (ddd, J=8.1, 6.6, 0.9, 1H), 6.70 (m, 2H), 3.57 (s, 3H), 2.99 (s, 6H), 2.71 (s, 3H).

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding 50 uL of 1N HCl
  3. additionIt was diluted with 50 mL of ethyl acetate
  4. washwashed with saturated sodium bicarbonate
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (25% ethyl acetate/hexanes) on silica gel

Sources & evidence

ORD record
ord-887499dd8a4f4535a1803e690538fe01
Source dataset
uspto-grants-2012_11
Patent number
US08309562B2

Reaction notes

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