Diisopropylethylamine → 6-((1R,2R)-2-hydroxycyclopentylamino)-5-methyl-3-(phenylamino)-2H-pyrazolo[3,4-d]pyrimidin-4(5H)-one

HRID 2389457Notes

Reaction equation

HRID 2389457 reaction equation
Cl[C:2]1[N:3]([CH3:19])[C:4](=[O:18])[C:5]2[C:10]([NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:9][NH:8][C:6]=2[N:7]=1.Cl.[NH2:21][C@@H:22]1[CH2:26][CH2:25][CH2:24][C@H:23]1[OH:27].CCN(C(C)C)C(C)C>CN(C=O)C>[OH:27][C@@H:23]1[CH2:24][CH2:25][CH2:26][C@H:22]1[NH:21][C:2]1[N:3]([CH3:19])[C:4](=[O:18])[C:5]2[C:6](=[N:8][NH:9][C:10]=2[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12886906(1R,2R)-2-aminocyclopentan-1-ol hydrochlorideHCID 178480563HCID 178480563, compound

Product 1

HCID 684983116-((1R,2R)-2-hydroxycyclopentylamino)-5-methyl-3-(phenylamino)-2H-pyrazolo[3,4-d]pyrimidin-4(5H)-oneYield 85.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-chloro-5-methyl-3-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one (3.3 g, 12 mmol), (1R,2R)-2-aminocyclopentanol hydrochloride (2 g, 14.4 mmol) and DIPEA (4.6 mL, 27 mmol) in DMF (25 mL) is heated at 120° C. for 5 hours. Solvent is removed under reduced pressure. The residue is dissolved in CH2Cl2 and MeOH (10:1, v/v), and then washed with water three times. The solution is dried over MgSO4 and evaporated to dryness to give 3.5 g of crude product. MS (ESI) m/z 341.2 [M+H]+.

Workup

  1. customSolvent is removed under reduced pressure
  2. dissolutionThe residue is dissolved in CH2Cl2
  3. washMeOH (10:1, v/v), and then washed with water three times
  4. dry with materialThe solution is dried over MgSO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-98690b0a990046058b03c2bd476c1767
Source dataset
uspto-grants-2012_09
Patent number
US08273751B2

Reaction notes

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