Ethanol → HCID 59519261, compound

HRID 237394Notes

Reaction equation

HRID 237394 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)[C:5]2[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[S:8][C:6]=2[N:7]=1.S(=O)(=O)(O)O.O.[CH2:29](O)[CH3:30]>>[CH2:29]([O:12][C:11]([C:9]1[S:8][C:6]2[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[NH:16][CH:15]=3)[C:5]=2[CH:10]=1)=[O:13])[CH3:30]

Participants

5

Reactant 4

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 59519199HCID 59519199, compound

Product 1

HCID 59519261HCID 59519261, compound

Procedure

The crude 2-amino-4-(1H-indol-3-yl)-thieno[2,3-d]pyrimidine-6-carboxylic acid was dissolved in ethanol (2 ml) and conc. sulphuric acid was added (5 drops). The solution was refluxed overnight before water was added and the volatiles were removed in vacuo. The aqueous solution was partitioned with 1M sodium hydrogen carbonate solution and ethyl acetate. The organics were combined, dried over sodium sulphate and evaporated to dryness. The pure compounds was obtained after preparative TLC as an off white coloured powder.

Workup

  1. additionwas added
  2. customthe volatiles were removed in vacuo
  3. customThe aqueous solution was partitioned with 1M sodium hydrogen carbonate solution and ethyl acetate
  4. dry with materialdried over sodium sulphate
  5. customevaporated to dryness
  6. customThe pure compounds was obtained after preparative TLC as

Sources & evidence

ORD record
ord-a92a2cea48144c8ab81f2834d3288285
Source dataset
uspto-grants-2014_02
Patent number
US08642594B2

Reaction notes

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