Lithium Hydroxide → HCID 86709677, compound

HRID 2285386Notes

Reaction equation

HRID 2285386 reaction equation
C[O:2][C:3](=[O:29])[C:4]([CH3:28])([CH3:27])/[CH:5]=[CH:6]/[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[N:12][C:13]([CH:17]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH3:18])=[N:14]2)=[CH:9][CH:8]=1.[OH-].[Li+]>O1CCCC1.O>[C:23]([Si:20]([CH3:22])([CH3:21])[O:19][CH:17]([C:13]1[N:12]=[CH:11][C:10]2[C:15](=[CH:16][C:7](/[CH:6]=[CH:5]/[C:4]([CH3:28])([CH3:27])[C:3]([OH:29])=[O:2])=[CH:8][CH:9]=2)[N:14]=1)[CH3:18])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86709678HCID 86709678, compound

Product 1

HCID 86709677HCID 86709677, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (E)-4-{2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-quinazolin-7-yl}-2,2-dimethyl-but-3-enoic acid methyl ester (1.07 g, 2.58 mmol) in tetrahydrofuran (50 mL) was cooled to 0° C. before adding an aqueous solution of lithium hydroxide (1 M, 8 mL, 8 mmol). The reaction mixture was allowed to warm to room temperature and was stirred for 20 h. The reaction mixture was diluted with water (50 mL) then washed with diethyl ether (60 mL) before acidifying to pH 2 with a saturated solution of potassium bisulfate. The resulting mixture was extracted with diethyl ether (3×30 mL). The extract was dried over anhydrous sodium sulfate, filtered and evaporated to yield the title product (0.605 g, 59%) as a yellow gum. 1H NMR (300 MHz, CDCl3) δ 0.06 (s, 3H), 0.08 (s, 3H), 0.90 (s, 9H), 1.53 (s, 6H), 1.64 (d, J=6.5 Hz, 3H), 5.22 (q, J=6.5 Hz, 1H), 6.64-6.81 (m, 2H), 7.73, 7.87 (ABq, J=8.5 Hz, 2H), 7.99 (s, 1H), 9.40 (s, 1H). LCMS (m/z) 401.2 [M+H], Tr=3.43 min.

Workup

  1. washthen washed with diethyl ether (60 mL)
  2. extractionThe resulting mixture was extracted with diethyl ether (3×30 mL)
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-d8c425d09c144a2eb0a29ba5ddb12ee1
Source dataset
uspto-grants-2015_09
Patent number
US09145441B2

Reaction notes

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