Tetrahydrofuran → HCID 131735537, compound

HRID 522643Notes

Reaction equation

Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])(C)C)=[O:15])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[Br-].[CH2:22]([Zn+])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH2:30]1COC[CH2:31]1>C(OCC)(=O)C.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>[CH2:22]([C:2]1[CH:7]=[N:6][C:5]([N:8]2[CH2:9][CH2:10][N:11]([C:14]([O:16][CH2:17][CH2:20][CH2:30][CH3:31])=[O:15])[CH2:12][CH2:13]2)=[N:4][CH:3]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of tert-butyl 4-(5-bromopyrimidin-2-yl)piperazine-1-carboxylate (12.0 g, 35.0 mmol) and tetrakis(triphenylphosphine)palladium (2.0 g, 1.7 mmol) in THF (200 mL, dry) was added dropwise a solution of benzylzinc(II) bromide in THF (140 mL, 0.5 M, 70 mmol). The reaction mixture was stirred at 70° C. for 4 h under N2, cooled to RT, then diluted with ethyl acetate (300 mL), filtered and concentrated. The residue was purified by silica gel chromatography, eluting with ethyl acetate/petroleum ether=1/20˜1/10, to give -butyl 4-(5-benzylpyrimidin-2-yl)piperazine-1-carboxylate (7.5 g, yield 60%) as a white solid, MS (ES+) C20H26N4O2 requires: 354, found: 355 [M+H]+.

Workup

temperaturecooled to RT
filtrationfiltered
concentrationconcentrated
customThe residue was purified by silica gel chromatography
washeluting with ethyl acetate/petroleum ether=1/20˜1/10

Sources & evidence

ORD record: ord-1105725cef674ce7885b59636555d562
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334263B2

Reaction notes

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