Dimethylformamide → HCID 10416328, compound

HRID 1785177Notes

Reaction equation

HRID 1785177 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[O:11]1[CH2:15][CH2:14]CC1.[Br:16][C:17]1[CH:25]=[C:24]([C:26]#[C:27][CH2:28][O:29][CH3:30])[C:20]2[O:21][CH2:22][O:23][C:19]=2[C:18]=1[NH2:31].Cl[C:33]1[C:42]2[C:37](=[CH:38][C:39]([O:45][CH2:46][CH2:47][CH2:48]Cl)=[C:40]([O:43][CH3:44])[CH:41]=2)[N:36]=[CH:35][N:34]=1.[Cl-].[NH4+:51].CCC[CH:55]([CH3:57])C.C[N:59]([CH3:62])C=O>C(OCC)(=O)C>[Br:16][C:17]1[CH:25]=[C:24]([C:26]#[C:27][CH2:28][O:29][CH3:30])[C:20]2[O:21][CH2:22][O:23][C:19]=2[C:18]=1[NH:31][C:33]1[C:42]2[C:37](=[CH:38][C:39]([O:45][CH2:46][CH2:47][CH2:48][N:51]3[CH2:57][CH2:55][N:59]([CH3:62])[C:15](=[O:11])[CH2:14]3)=[C:40]([O:43][CH3:44])[CH:41]=2)[N:36]=[CH:35][N:34]=1

Participants

9

Reactant 7

HCID 6228DimethylformamideHCID 78922-MethylpentaneHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 574472274-Chloro-7-(3-chloropropoxy)-6-methoxyquinazolineHCID 68882346HCID 68882346, compound

Product 1

HCID 10416328HCID 10416328, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of sodium bis(trimethylsilyl)amide (0.5 ml) in tetrahydrofuran (1.0M, 0.5 mmol) was added dropwise to an ice-cold solution of [5-bromo-7-(3-methoxyprop-1-yn-1-yl)-1,3-benzodioxol-4-yl]amine (0.073 g, 0.25 mmol) and 4-chloro-7-(3-chloropropoxy)-6-methoxyquinazoline (0.076 g, 0.26 mmol) in dimethylformamide (5 ml). The mixture was allowed to warm to room temperature over 2 hours and then stirred at room temperature overnight. A saturated solution of ammonium chloride (15 ml) was added and the mixture was extracted with ethyl acetate (15 ml). The organic layer was separated, washed with a saturated solution of sodium chloride (25 ml), dried over magnesium sulfate and evaporated under reduced pressure to leave a brown oil. Flash chromatography on silica eluting with a mixture of 1:1 to 3:1 ethyl acetate and iso-hexane gave the product as a brown gum (0.066 g). Mass Spectrum: M+H+ 534/536/538.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (15 ml)
  2. customThe organic layer was separated
  3. washwashed with a saturated solution of sodium chloride (25 ml)
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customto leave a brown oil

Sources & evidence

ORD record
ord-3401318c08d849d3a0dc22f4f2e93226
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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