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

HRID 222066Notes

Reaction equation

HRID 222066 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) δ2.14 (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-e1d18320af4d4f37bd669c2259ee3ec6
Source dataset
uspto-grants-2012_06
Patent number
US08207178B2

Reaction notes

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