Diethyl Ether → HCID 66617862, compound

HRID 559449Notes

Reaction equation

[CH3:1][C@H:2]1[C:10]2[C:9]([N:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)=[N:8][CH:7]=[N:6][C:5]=2[C:4](=[O:24])[CH2:3]1.C[Li].[CH2:27](OCC)C>C1COCC1>[OH:24][C:4]1([CH3:27])[C:5]2[N:6]=[CH:7][N:8]=[C:9]([N:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[C:10]=2[C@H:2]([CH3:1])[CH2:3]1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of (R)-tert-butyl 4-(5-methyl-7-oxo-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate (40 mg, 0.120 mmol) in THF (4 mL) was added to a 1.5M solution of methyllithium in diethyl ether (0.088 mL, 0.132 mmol) at −78° C. The resulting mixture was stirred at −78° C. for 1 hour and quenched by saturated aqueous NH4Cl. The aqueous layer was extracted with EtOAc (2×). The organic layer was dried (MgSO4) and concentrated. The residue was purified by a silica cartridge (5.0 g) eluted by EtOAc to give tert-butyl 4-((5R)-7-hydroxy-5,7-dimethyl-6,7-dihydro-5H -cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate as an off-white solid (29 mg, 69%). LCMS (APCI+) [M-Boc+H]+ 349.1; Rt: 2.49 mm.

Workup

customquenched by saturated aqueous NH4Cl
extractionThe aqueous layer was extracted with EtOAc (2×)
dry with materialThe organic layer was dried (MgSO4)
concentrationconcentrated
customThe residue was purified by a silica cartridge (5.0 g)
washeluted by EtOAc

Sources & evidence

ORD record: ord-8c1781f0433548b983802038f7774f3f
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063050B2

Reaction notes

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