(S)-(+)-1-Aminopropan-2-ol → HCID 178503500, compound

HRID 2114579Notes

Reaction equation

HRID 2114579 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]2[NH:10][N:11]=[C:12]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)[C:3]=12.[NH2:18][CH2:19][C@@H:20]([OH:22])[CH3:21]>C1COCC1>[CH:13]1([C:12]2[C:3]3[C:4](=[N:5][C:6]([S:8][CH3:9])=[N:7][C:2]=3[NH:18][CH2:19][C@H:20]([OH:22])[CH3:21])[NH:10][N:11]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 2

HCID 7311736(S)-(+)-1-Aminopropan-2-olHCID 178503464HCID 178503464, compound

Product 1

HCID 178503500HCID 178503500, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-3-cyclopentyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidine (500 mg, 1.860 mmol) was dissolved in 25 mL dry THF, and (S)-1-Amino-propan-2-ol (1.758 mL, 22.32 mmol) was added. The reaction mixture was heated to reflux for three hours, then cooled to room temperature. The reaction mixture was partitioned between water and ethyl acetate, and the organic phase was separated, washed with water, washed with brine, dried (MgSO4), filtered and evaporated under reduced pressure to give 0.56 g of (R)-1-(3-Cyclopentyl-6-methylsulfanyl-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)-propan-2-ol. Mass Spec. M+H=309.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for three hours
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. customthe organic phase was separated
  5. washwashed with water
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-4a73f8ff63df44119e066dab854cd04f
Source dataset
uspto-grants-2008_10
Patent number
US07435731B2

Reaction notes

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