Dimethyl Sulfoxide → 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-2-cyclopenten-1-ol

HRID 898053Notes

Reaction equation

HRID 898053 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[NH:4][N:3]=1.CS(C)=O.[O:16]1[CH:18]2[CH2:19][CH:20]=[CH:21][CH:17]12>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([CH:20]3[CH2:21][CH:17]([OH:16])[CH:18]=[CH:19]3)[N:3]=[C:2]([I:1])[C:10]=12

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 1655746-Oxabicyclo[3.1.0]hex-2-eneHCID 178508725HCID 178508725, compound

Product 1

HCID 223473184-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-2-cyclopenten-1-olYield 61.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tetrakis(triphenylphosphine)palladium(0) (0.04 g, 0.03 mmol), 3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.30 g, 1.14 mmol) and dimethyl sulfoxide (3 mL) was stirred at ambient temperature in the dark for 2 minutes and cooled to 0° C. A solution of 2,4a-dihydro-1aH-cyclopenta[b]oxirene (0.14 g, 1.72 mmol) in tetrahydrofuran (3 mL) was added into the mixture at 0° C. and stirred at 0° C. for 3 hours. The mixture was stirred at ambient temperature overnight and purified by preparative HPLC to yield 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-2-cyclopenten-1-ol (0.24 g, 0.70 mmol) as a white solid: RP-HPLC (Hitachi HPLC, Hypersil C18, 5 μm, 100 A, 250×4.6 mm; 25%-100% acetonitrile-0.05M ammonium acetate over 10 min, 1 mL/min) Rt 4.23 min. MS: MH+ 344.

Workup

  1. temperaturecooled to 0° C
  2. stirringstirred at 0° C. for 3 hours
  3. stirringThe mixture was stirred at ambient temperature overnight
  4. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-c48730d82b3f439bb8e9bb24c1cdd033
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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