HCID 59519299, compound → HCID 59519279, compound

HRID 237396Notes

Reaction equation

HRID 237396 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:26][C:9]2[N:10]=[C:11]([NH2:25])[N:12]=[C:13]([C:14]([C:16]3[CH:24]=[CH:23][C:19]4[O:20][CH2:21][O:22][C:18]=4[CH:17]=3)=[O:15])[C:8]=2[CH:7]=1)=[O:5])[CH3:2].[CH3:27][Mg]Br>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[S:26][C:9]2[N:10]=[C:11]([NH2:25])[N:12]=[C:13]([C:14]([C:16]3[CH:24]=[CH:23][C:19]4[O:20][CH2:21][O:22][C:18]=4[CH:17]=3)([OH:15])[CH3:27])[C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 59519299HCID 59519299, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 59519279HCID 59519279, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

2-Amino-4-(benzo[1,3]dioxole-5-carbonyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (example 312) (100 mg) was dissolved in anhydrous THF under a nitrogen atmosphere before methyl magnesium bromide (3.0M solution in diethyl ether, 5 equiv.) was added. The solution was stirred at 40° C. overnight before being partitioned between 10% aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulphate and evaporated to yield a crude product that was purified by preparative TLC to give the desired compound as a yellow powder.

Workup

  1. additionwas added
  2. custombefore being partitioned between 10% aqueous ammonium chloride solution and ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customto yield a crude product that
  7. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-ce4f19be061249f084714799a5167997
Source dataset
uspto-grants-2014_02
Patent number
US08642594B2

Reaction notes

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