Sodium hydride → 4-(2,6-Dimethyl-4-(pyridin-4-yl)phenoxy)-6-chloro-1H-pyrazolo[3,4-d]pyrimidine

HRID 222091Notes

Reaction equation

HRID 222091 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[CH:7]=[C:6]([CH3:16])[C:5]=1[OH:17].Cl[C:19]1[N:24]=[C:23]([Cl:25])[N:22]=[C:21]2[NH:26][N:27]=[CH:28][C:20]=12>>[CH3:3][C:4]1[CH:9]=[C:8]([C:10]2[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=2)[CH:7]=[C:6]([CH3:16])[C:5]=1[O:17][C:19]1[N:24]=[C:23]([Cl:25])[N:22]=[C:21]2[NH:26][N:27]=[CH:28][C:20]=12

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 120664494,6-Dichloro-1H-pyrazolo(3,4-d)pyrimidineHCID 1361102652,6-Dimethyl-4-(pyridin-4-yl)phenol

Product 1

HCID 577474064-(2,6-Dimethyl-4-(pyridin-4-yl)phenoxy)-6-chloro-1H-pyrazolo[3,4-d]pyrimidine

Procedure

Sodium hydride (1.2 eq) is added to 2,6-dimethyl-4-(pyridin-4-yl)phenol (prepared according to literature procedures, see Combellas et al., Tetrahedron Letters, 1992, 33, 4923) (1.2 eq) in 1-methyl-2-pyrridone (2 ml/mmol) at 0° C. The reaction mixture is stirred at room temperature for 30 min and a solution of 4,6-dichloro-1H-pyrazolo[3,4-d]pyrimidine (1 eq) in 1-methyl-2-pyrridone (1 ml/mmol) is added. The resulting mixture is heated to 100° C. for 16 h, cooled to room temperature, poured into ice water and extracted with CHCl3 (×3). The combined organic layers are washed with water and brine, dried (Na2SO4), concentrated to dryness and purified by silica gel chromatography.

Workup

  1. temperatureThe resulting mixture is heated to 100° C. for 16 h
  2. temperaturecooled to room temperature
  3. extractionextracted with CHCl3 (×3)
  4. washThe combined organic layers are washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated to dryness
  7. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-13b350c4af244183a627858341013c9b
Source dataset
uspto-grants-2012_06
Patent number
US08207178B2

Reaction notes

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