Sodium Carbonate → HCID 135702869, compound

HRID 566328Notes

Reaction equation

HRID 566328 reaction equation
O.[NH2:2][C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1.Br[C:13]1[CH:42]=[CH:41][C:16]([CH2:17][C:18]2[NH:19][C:20](=[O:40])[C:21]3[C:26]([CH2:27][CH3:28])=[N:25][N:24]([CH:29]([CH3:39])[CH2:30][CH2:31][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)[C:22]=3[N:23]=2)=[CH:15][CH:14]=1.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>[NH2:2][C:3]1[CH:4]=[C:5]([C:13]2[CH:42]=[CH:41][C:16]([CH2:17][C:18]3[NH:19][C:20](=[O:40])[C:21]4[C:26]([CH2:27][CH3:28])=[N:25][N:24]([CH:29]([CH3:39])[CH2:30][CH2:31][CH2:32][C:33]5[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=5)[C:22]=4[N:23]=3)=[CH:15][CH:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 143894233-Aminophenylboronic acid monohydrateHCID 135479984HCID 135479984, compound

Product 1

HCID 135702869HCID 135702869, compoundYield 6.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

697 mg (4.5 mmol) of 3-aminophenylboronic acid monohydrate and 150 mg of tetrakistriphenylphosphine-palladium are added under argon to a solution of 1.66 g (3.47 mmol) of 6-(4-bromo-benzyl)-1-(1-methyl-4-phenyl-butyl)-3-ethyl-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one in 38 ml of THF, and the mixture is stirred for one hour at 70° C. After 4.9 ml of 1N Na2CO3 solution have been added, the mixture is stirred for a further 4 hours at 70° C., the solvent is removed in vacuo, and the residue is 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 extract 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. customthe solvent is removed in vacuo
  3. extractionThe mixture is extracted with 2N HCl
  4. extractionextracted twice with CH2Cl2
  5. dry with materialAfter the extract has been dried over Na2SO4
  6. customthe solvent is removed in vacuo
  7. customPurification by chromatography (toluene/ethyl acetate=4:1)

Sources & evidence

ORD record
ord-f9fb7525a54e4bbdb21da2327a7c034f
Source dataset
uspto-grants-2001_01
Patent number
US06174884B1

Reaction notes

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