HCID 178419772, compound → HCID 178517895, compound

HRID 522682Notes

Reaction equation

HRID 522682 reaction equation
Br[C:2]1[C:3]([OH:21])=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11](C(OC(C)(C)C)=O)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[Br-].[CH2:23]([Zn+])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1.C(OCC)(=O)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[CH2:23]([C:2]1[C:3]([OH:21])=[N:4][C:5]([N:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]2)=[N:6][CH:7]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 2

HCID 178419772HCID 178419772, compoundHCID 178452260HCID 178452260, compound

Product 1

HCID 178517895HCID 178517895, compoundYield 54.2%

Reagents, catalysts & solvents 3

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)CatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 4-(5-bromo-4-hydroxypyrimidin-2-yl)piperazine-1-carboxylate (20 g, 56 mmol) and Pd(Amphos)Cl2 (4.0 g 5.6 mmol) in THF (200 mL, dry) was added benzylzinc(II) bromide (168 mL, 168 mmol) under argon and the mixture was stirred at 60° C. overnight. The reaction mixture was diluted with ethyl acetate (1.5 L), filtered and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (petroleum ether/ethyl acetate=1:1 to 100% ethyl acetate) to give 5-benzyl-2-(piperazin-1-yl)pyrimidin-4-ol (8.2 g, 54%) as a pale yellow solid. MS (ES+) C15H18N4O requires: 270, found: 271 [M+H]+.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (petroleum ether/ethyl acetate=1:1 to 100% ethyl acetate)

Sources & evidence

ORD record
ord-8274958f573348e6864c48c032bc408d
Source dataset
uspto-grants-2016_05
Patent number
US09334263B2

Reaction notes

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