Sodium Carbonate → HCID 135702865, compound

HRID 566338Notes

Reaction equation

HRID 566338 reaction equation
C(B(CC)[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1)C.[C:12]([CH:15]([N:25]1[C:29]2[N:30]=[C:31]([CH2:35][C:36]3[CH:41]=[CH:40][C:39](Br)=[CH:38][CH:37]=3)[NH:32][C:33](=[O:34])[C:28]=2[CH:27]=[N:26]1)[CH2:16][CH2:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:14])[CH3:13].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.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>[C:12]([CH:15]([N:25]1[C:29]2[N:30]=[C:31]([CH2:35][C:36]3[CH:37]=[CH:38][C:39]([C:4]4[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=4)=[CH:40][CH:41]=3)[NH:32][C:33](=[O:34])[C:28]=2[CH:27]=[N:26]1)[CH2:16][CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)(=[O:14])[CH3:13]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 6428513-(Diethylboryl)pyridine2×HCID 135702886HCID 135702886, compound

Product 1

HCID 135702865HCID 135702865, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

71 mg (0.48 mmol) of diethyl-(3-pyridyl)-borane and 16 mg of tetrakistriphenylphosphine-palladium are added under argon to a solution of 177 mg (0.37 mmol) of 1-(1-acetyl-4-phenyl-butyl)-6-(4-bromo-benzyl)-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one in 4 ml of THF, and the mixture is stirred for one hour at 70° C. After 0.522 ml of 2 N Na2CO3 solution have been added, the mixture is stirred for a further 4 hours at 70° C., a further 27 mg (0.185 mmol) of diethyl-(3-pyridyl)-borane and 16 mg of tetrakistriphenylphosphine-palladium are added, and the mixture is stirred for 14 hours under reflux. The solvent is removed in vacuo and the residue taken up in CH2Cl2. The mixture is extracted with 2N HCl, and the aqueous phase is rendered alkaline with 1N NaOH and extracted twice with CH2Cl2. After the mixture has been dried over Na2SO4, the solvent is removed in vacuo. Purification by chromatography (toluene/ethyl/acetate=4:1) gives 110 mg (6.4%) of a pale yellow solid.

Workup

  1. stirringthe mixture is stirred for a further 4 hours at 70° C.
  2. stirringthe mixture is stirred for 14 hours
  3. temperatureunder reflux
  4. customThe solvent is removed in vacuo
  5. extractionThe mixture is extracted with 2N HCl
  6. extractionextracted twice with CH2Cl2
  7. dry with materialAfter the mixture has been dried over Na2SO4
  8. customthe solvent is removed in vacuo
  9. customPurification by chromatography (toluene/ethyl/acetate=4:1)

Sources & evidence

ORD record
ord-522d66e7d3a94ea3b963bb452f388ea1
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Reaction notes

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