Sodium hydride → 2-chloro-N-(5-chloro-1,3-benzodioxol-4-yl)pyrimidin-4-amine

HRID 2237406

Reaction equation

HRID 2237406 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[CH:11][C:7]2[O:8][CH2:9][O:10][C:6]=2[C:5]=1[NH2:13].[Cl:14][C:15]1[N:20]=[C:19](Cl)[CH:18]=[CH:17][N:16]=1>CC(N(C)C)=O>[Cl:14][C:15]1[N:20]=[C:19]([NH:13][C:5]2[C:6]3[O:10][CH2:9][O:8][C:7]=3[CH:11]=[CH:12][C:4]=2[Cl:3])[CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 775312,4-DichloropyrimidineHCID 113672535-Chloro-1,3-benzodioxol-4-amine

Product 1

HCID 426316842-chloro-N-(5-chloro-1,3-benzodioxol-4-yl)pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

Sodium hydride (13.4 g, 60% dispersion in mineral oil) was added portionwise to (5-chloro-1,3-benzodioxol-4-yl)amine (11.5 g, prepared as described in WO2001094341) in DMA (100 ml) at 0° C. 2,4-Dichloropyrimidine (10 g) was added and the reaction warmed to room temperature and stirred overnight. The reaction was quenched cautiously with water, the solution filtered and concentrated and the residue dissolved in DCM, washed with water and brine, dried and concentrated to give 2-chloro-N-(5-chlorobenzo[d][1,3]dioxol-4-yl)pyrimidin-4-amine as a dark brown oil that was used without further purification (16 g, 85%); NMR Spectrum (300 MHz, DMSO) 6.10 (s, 2H), 6.58 (d, 1H), 6.94 (d, 1H), 7.05 (d, 1H), 8.15 (d, 1H), 9.76 (s, 1H); Mass Spectrum M+ 284.

Workup

  1. customThe reaction was quenched cautiously with water
  2. filtrationthe solution filtered
  3. concentrationconcentrated
  4. dissolutionthe residue dissolved in DCM
  5. washwashed with water and brine
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f82a01ee902b4b9bab48dbf01b09e4c3
Source dataset
uspto-grants-2010_05
Patent number
US07718653B2

Linked notes

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