tert-Butoxy bis(dimethylamino)methane → HCID 57747332, compound

HRID 386622Notes

Reaction equation

HRID 386622 reaction equation
[Br:1][C:2]1[CH:27]=[C:26]([CH3:28])[C:5]([O:6][C:7]2[C:12]([N+:13]([O-:15])=[O:14])=[C:11]([CH3:16])[N:10]=[C:9]([NH:17][C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=3)[N:8]=2)=[C:4]([CH3:29])[CH:3]=1.C(O[CH:35](N(C)C)[N:36]([CH3:38])[CH3:37])(C)(C)C>CN(C=O)C>[Br:1][C:2]1[CH:27]=[C:26]([CH3:28])[C:5]([O:6][C:7]2[C:12]([N+:13]([O-:15])=[O:14])=[C:11](/[CH:16]=[CH:35]/[N:36]([CH3:38])[CH3:37])[N:10]=[C:9]([NH:17][C:18]3[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=3)[N:8]=2)=[C:4]([CH3:29])[CH:3]=1

Participants

4

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 57747433HCID 57747433, compound

Product 1

HCID 57747332HCID 57747332, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a homogenous mixture of 4-(4-(4-bromo-2,6-dimethylphenoxy)-6-methyl-5-nitropyrimidin-2-ylamino)benzonitrile (22.71 g, 50 mmol) in DMF (300 ml) was added tert-butoxybis (dimethylamino) methane (12.39 ml, 60 mmol) over 15 minutes. The mixture was stirred at room temperature overnight. DMF was partially removed. The residue was washed with water and extracted with ethyl acetate (×3). The organic layers were combined, washed with brine, dried (MgSO4) and concentrated to dryness yielding to the desired product as a yellow solid (23.41 g, 46.0 mmol, 92%) which was used in next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 2.14 (s, 6H), 2.98 (bs, 3H), 3.13 (bs, 3H), 5.54 (d, J=12.4 Hz, 1H), 7.03 (s, 1H), 7.27 (d, J=8.6, 2H), 7.28 (s, 2H), 7.40 (d, J=8.6, 2H), 8.03 (d, J=12.2 Hz, 1H).

Workup

  1. customDMF was partially removed
  2. washThe residue was washed with water
  3. extractionextracted with ethyl acetate (×3)
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5ad4810cd065418e90ee5f2d653b0193
Source dataset
uspto-grants-2013_02
Patent number
US08372852B2

Reaction notes

Loading…