Methanol → HCID 59442119, compound

HRID 1014515Notes

Reaction equation

HRID 1014515 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1C(=O)[N:5]1[C:15]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][N:26]([CH:29]([CH3:31])[CH3:30])[CH2:25][CH2:24]4)=[CH:19][C:18]=3[O:32][CH3:33])=[N:14][C:13]3[N:34]([S:37]([C:40]4[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=4)(=[O:39])=[O:38])[CH:35]=[CH:36][C:12]=3[C:6]1=[N:7]2.[C:48](=[O:51])([O-])[O-:49].[K+].[K+].[CH3:54]O>>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:7][C:6]2[C:12]3[CH:36]=[CH:35][N:34]([S:37]([C:40]4[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=4)(=[O:39])=[O:38])[C:13]=3[N:14]=[C:15]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([N:23]4[CH2:28][CH2:27][N:26]([CH:29]([CH3:31])[CH3:30])[CH2:25][CH2:24]4)=[CH:19][C:18]=3[O:32][CH3:33])[N:5]=2)[C:3]=1[C:48]([O:49][CH3:54])=[O:51]

Participants

4

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 59442078HCID 59442078, compound

Product 1

HCID 59442119HCID 59442119, compoundYield 80%

Procedure

A solution of 8-bromo-5-{[4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)phenyl]amino}-3-[(4-methylphenyl)sulfonyl]pyrrolo[2′,3′:4,5]pyrimido[6,1-b]quinazolin-7(3H)-one (120 mg, 0.167 mmol), and potassium carbonate (69.4 mg, 0.502 mmol) in methanol (25 ml) was stirred at room temperature. The reaction was filtered to remove the base, organic layer was filtered through a cotton plug, concentrated by rotary evaporation, adsorbed onto silica gel, and purified by silica gel chromatography (DCM to 10% MeOH/DCM) to give methyl 2-bromo-6-({2-{[4-[4-(1-methylethyl)-1-piperazinyl]-2-(methyloxy)phenyl]amino}-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidin-4-yl}amino)benzoate (0.1 g, 80%). ESIMS (M+H)+=748.

Workup

  1. filtrationThe reaction was filtered
  2. customto remove the base, organic layer
  3. filtrationwas filtered through a cotton plug
  4. concentrationconcentrated by rotary evaporation
  5. custompurified by silica gel chromatography (DCM to 10% MeOH/DCM)

Sources & evidence

ORD record
ord-95c945c46fdc461bae337b0384dd46d3
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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