Ethanolamine → HCID 21098029, compound

HRID 1351150Notes

Reaction equation

HRID 1351150 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[N:6][C:7](S(C)(=O)=O)=[N:8][CH:9]=2)[N:4]([CH3:15])[N:3]=1.[CH2:16]([CH2:18][NH2:19])[OH:17].O.C(OCC)(=O)C>CN1CCCC1=O>[Cl:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([NH:19][CH2:18][CH2:16][OH:17])=[N:8][CH:9]=2)[N:4]([CH3:15])[N:3]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 962WaterHCID 8857Ethyl AcetateHCID 21098061HCID 21098061, compound

Product 1

HCID 21098029HCID 21098029, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-chloro-6-methanesulfonyl-1-methyl-1H-pyrazolo[3,4-d]pyrimidine (131 mg, 0.5 mmol) in 1-methyl-2-pyrrolidinone (5 mL) was added ethanolamine (150 mg, 2.5 mmol, 5 eq) and the reaction mixture was heated to 50° C. After 1 hour, water (20 mL) was added, followed by ethyl acetate (20 mL). The layers were separated. The organic layer was washed with brine, dried over MgSO4, filtered and evaporated. The resulting yellow residue was purified by column chromatography (50% ethyl acetate-hexane) to give 2-(3-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamino)-ethanol (100 mg, 87% yield); LC/MS (m/e)=228.2 (MH+), Rt=1.44 min.

Workup

  1. customThe layers were separated
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe resulting yellow residue was purified by column chromatography (50% ethyl acetate-hexane)

Sources & evidence

ORD record
ord-ee85d74b466c4f36addda736eb55ffaa
Source dataset
uspto-grants-2007_05
Patent number
US07217710B2

Reaction notes

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