tert-Butyl bromoacetate → HCID 86754363, compound

HRID 1584545Notes

Reaction equation

HRID 1584545 reaction equation
C([Li])CCC.[N:6]1([C:11]2[N:12]=[C:13]([N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[NH:16][C:15]=3[N:23]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1.Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32]>C1COCC1>[N:6]1([C:11]2[N:12]=[C:13]([N:24]3[CH2:25][CH2:26][CH2:27][CH2:28]3)[C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[C:15]=3[N:23]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 15521617HCID 15521617, compoundHCID 178418339Butyllithium

Product 1

HCID 86754363HCID 86754363, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyllithium (4.26 mL; 1.6 M in hexane) is added to a mixture of 2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole (III, EXAMPLE 2, 2.0 g) in THF (50 mL) at -15°. After 1 hr, t-butyl bromoacetate (1.27 g) in THF (20 mL) is added, and the mixture is stirred for 2 hr at 20-25°. The mixture is partitioned between aqueous sodium bicarbonate and methylene chloride, and the organic layer is dried and concentrated. Chromatography of the crude product (silica gel; hexane/methylene chloride/ethyl acetate (70/25/5) gives the title compound, mp=131-133°; NMR (CDCl3) 7.87, 7.15, 4.92, 3.92, 3.61, 1.96 and 1.43 δ; MS (m/z=421 (M+).

Workup

  1. customThe mixture is partitioned between aqueous sodium bicarbonate and methylene chloride
  2. customthe organic layer is dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-34c86e5a1cdc45edaaa038d66805d63a
Source dataset
uspto-grants-1999_08
Patent number
US05932728

Reaction notes

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