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1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → (S)-2-(biphenyl-4-ylmethyl)-7-isobutyl-5-methyl-3-(pyrrolidin-3-ylamino)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

HRID 81415
Notes
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Reaction equation

HRID 81415 reaction equation
[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:16](Cl)=[C:15]3[C:10]([N:11]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:12](=[O:20])[N:13]([CH3:19])[C:14]3=[O:18])=[N:9]2)=[CH:3][CH:2]=1.[NH2:31][C@H:32]1[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(O[K])(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:1]1([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:16]([NH:31][C@H:32]3[CH2:36][CH2:35][NH:34][CH2:33]3)=[C:15]3[C:10]([N:11]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:12](=[O:20])[N:13]([CH3:19])[C:14]3=[O:18])=[N:9]2)=[CH:3][CH:2]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 854071tert-butyl (3S)-3-aminopyrrolidine-1-carboxylateHCID 685083002-(biphenyl-4-ylmethyl)-3-chloro-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dioneHCID 178418922HCID 178418922, compound

Product 1

HCID 42640996
(S)-2-(biphenyl-4-ylmethyl)-7-isobutyl-5-methyl-3-(pyrrolidin-3-ylamino)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
130 °C

Procedure

2-(biphenyl-4-ylmethyl)-3-chloro-7-isobutyl-5-methyl-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione (25 mg, 0.056 mmol) is dissolved in anhydrous and degassed THF, and then (S)-tert-butyl 3-aminopyrrolidine-1-carboxylate (64 mg, 0.34 mmol), Pd2(dba)3 (25 mg, 0.026 mmol) and Xantphos (16 mg, 0.026 mmol) are added, followed by tBuOK (7.5 mg, 0.067 mmol). The reaction mixture is heated in microwave at 130° C. for 2.5 h. After cooling, solvent is removed. The residue is diluted with ethyl acetate (50 mL), and then washed with sodium carbonate aqueous solution three times. Solvent is removed under reduced pressure, the residue is treated with 50% TFA in CH2Cl2 (v/v) at room temperature for 6 hours. Evaporation to remove TFA and solvent, and the residue is purified by a semi-preparative HPLC to give pure product. MS (ESI) m/z 473.2 [M+H]+.

Workup

  1. customdegassed THF
  2. temperatureAfter cooling
  3. customsolvent is removed
  4. additionThe residue is diluted with ethyl acetate (50 mL)
  5. washwashed with sodium carbonate aqueous solution three times
  6. customSolvent is removed under reduced pressure
  7. additionthe residue is treated with 50% TFA in CH2Cl2 (v/v) at room temperature for 6 hours
  8. customEvaporation
  9. customto remove TFA and solvent
  10. customthe residue is purified by a semi-preparative HPLC
  11. customto give pure product

Sources & evidence

ORD record
ord-ea4b18044c2a44c29d3eb328e111d7a5
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08846693B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes