Dimethylformamide → HCID 68882807, compound

HRID 1785175Notes

Reaction equation

HRID 1785175 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][CH:28]([O:30][CH3:31])[CH3:29])[C:20]2[O:21][CH2:22][O:23][C:19]=2[C:18]=1[NH2:32].Cl[C:34]1[C:43]2[C:38](=[CH:39][C:40]([O:46][CH2:47][CH2:48][CH2:49]Cl)=[C:41]([O:44][CH3:45])[CH:42]=2)[N:37]=[CH:36][N:35]=1.[Cl-].[NH4+:52].CCC[CH:56]([CH3:58])C.C[N:60]([CH3:63])C=O>C(OCC)(=O)C>[Br:16][C:17]1[CH:25]=[C:24]([C:26]#[C:27][CH:28]([O:30][CH3:31])[CH3:29])[C:20]2[O:21][CH2:22][O:23][C:19]=2[C:18]=1[NH:32][C:34]1[C:43]2[C:38](=[CH:39][C:40]([O:46][CH2:47][CH2:48][CH2:49][N:52]3[CH2:58][CH2:56][N:60]([CH3:63])[C:15](=[O:11])[CH2:14]3)=[C:41]([O:44][CH3:45])[CH:42]=2)[N:37]=[CH:36][N:35]=1

Participants

9

Reactant 7

HCID 6228DimethylformamideHCID 78922-MethylpentaneHCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 574472274-Chloro-7-(3-chloropropoxy)-6-methoxyquinazolineHCID 68882661HCID 68882661, compound

Product 1

HCID 68882807HCID 68882807, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of sodium bis(trimethylsilyl)amide (1.4 ml) in tetrahydrofuran (1.0M, 1.4 mmol) was added dropwise to an ice-cold solution of 5-bromo-7-(3-methoxybut-1-yn-1-yl)-1,3-benzodioxol-4-amine (0.208 g, 0.70 mmol) and 4-chloro-7-(3-chloropropoxy)-6-methoxyquinazoline (0.201 g, 0.70 mmol) in dimethylformamide (10 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 (25 ml) was added and the mixture was then extracted with ethyl acetate (25 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 1:1 to 3:1 mixture of ethyl acetate and iso-hexane gave the product as a brown gum (0.245 g).

Workup

  1. extractionthe mixture was then extracted with ethyl acetate (25 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-8859fcd3f88f459ea056c4b215b258a4
Source dataset
uspto-grants-2009_03
Patent number
US07504408B2

Reaction notes

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