2(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl- → HCID 69459163, compound

HRID 852420Notes

Reaction equation

HRID 852420 reaction equation
[Li+].CC([N-]C(C)C)C.[C:9]([O:13][C:14]([CH:16]1[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].[CH3:19][Si:20]([C:23]#[C:24][CH2:25]Br)([CH3:22])[CH3:21].CN1C(=O)N(C)CCC1>C1COCC1>[C:9]([O:13][C:14]([C:16]1([CH2:25][C:24]#[C:23][Si:20]([CH3:22])([CH3:21])[CH3:19])[CH2:18][CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 6425893-Bromo-1-(trimethylsilyl)-1-propyneHCID 2724682Lithium diisopropylamideHCID 13676038tert-Butyl cyclopropanecarboxylate

Product 1

HCID 69459163HCID 69459163, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of 14.0 ml (2.0 M in THF/n-heptane/ethylbenzene, 28 mmol) LDA in 100 ml THF was treated during 15 min at −78° C. with 2.84 g (20 mmol) cyclopropanecarboxylic acid tert-butyl ester in 20 ml THF. After 6 h at −78° C., a solution of 3-(trimethylsilyl) propargyl bromide and 29 ml DMPU in 40 ml THF was added during 20 min. Over night, the solution was naturally warmed to room temperature, poured on ice/aqueous saturated NH4Cl solution and extracted with ether (three times). The organic phases were washed with aqueous 10% KHSO4, water (5×), aqueous 10% NaCl and dried (Na2SO4) to give 5.59 g of the title compound as volatile dark brown liquid.

Workup

  1. waitOver night
  2. additionpoured on ice/aqueous saturated NH4Cl solution
  3. extractionextracted with ether (three times)
  4. washThe organic phases were washed with aqueous 10% KHSO4, water (5×), aqueous 10% NaCl
  5. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-0a29cbad4e334ed08a42e5ea7cdfd1b2
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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