Aluminium lithium hydride → HCID 58169454, compound

HRID 1484859Notes

Reaction equation

HRID 1484859 reaction equation
[Cl: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]>C1COCC1>[Cl: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

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58169488HCID 58169488, compound

Product 1

HCID 58169454HCID 58169454, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of ethyl 2-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidine-5-carboxylate (3.5 g, 11.4 mmol, 1.0 eq) in anhydrous THF (50 mL), LiAlH4 (1.3 g, 34.2 mmol, 3.0 eq) was added portionwise under 0° C. (ice bath). The mixture was stirred at 0° C. for 1 h and 20° C. for 16 h. Ice-water (50 mL) was added and the resulting mixture was extracted by EtOAc (4×50 mL). The combined organic phases were washed (brine), dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel chromatography (CH2Cl2/MeOH 500:1 to 15:1 as eluent) to afford (2-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-5-yl)methanol (350 mg, 12%) as white solid. LC-MS (m/z)=266.0 [M+H]+.

Workup

  1. extractionthe resulting mixture was extracted by EtOAc (4×50 mL)
  2. washThe combined organic phases were washed (brine)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (CH2Cl2/MeOH 500:1 to 15:1 as eluent)

Sources & evidence

ORD record
ord-992a455555c849ddb8af195c6444b180
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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