Aluminium lithium hydride → HCID 86651551, compound

HRID 1484941Notes

Reaction equation

HRID 1484941 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:16][CH2:15]3)[NH:11][N:10]=2)[C:5]([C:17](OCC)=[O:18])=[CH:4][N:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+].O>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([CH:14]3[CH2:15][CH2:16]3)[NH:11][N:10]=2)[C:5]([CH2:17][OH:18])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 21226445Aluminium lithium hydrideHCID 45051631Sodium sulphate hydrateHCID 58169573HCID 58169573, compound

Product 1

HCID 86651551HCID 86651551, compoundYield 17.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of ethyl 2-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidine-5-carboxylate (3.0 g, 8.5 mmol, 1 eq) in THF (300 ml) at −78° C., LiAlH4 (3.0 g) was added slowly. After stirring at RT for 1 h, Na2SO4.H2O was added and stirred at 23° C. for 0.5 h. The mixture was filtered and extracted with EtOAc (3×50 ml). The combined organic phases were washed (brine), dried (Na2SO4), filtered and concentrated to give a residue. The residue was purified by silica gel column chromatography (PE/EtOAc=1:1 as eluant) to give (2-bromo-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-5-yl)methanol (450 mg, 17.03%) as white solid. LC-MS (m/z)=311.15 [M+H]+

Workup

  1. stirringstirred at 23° C. for 0.5 h
  2. filtrationThe mixture was filtered
  3. extractionextracted with EtOAc (3×50 ml)
  4. washThe combined organic phases were washed (brine)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a residue
  9. customThe residue was purified by silica gel column chromatography (PE/EtOAc=1:1 as eluant)

Sources & evidence

ORD record
ord-aff63241566c45299bb427d0107fe3d1
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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