Ethanol → thieno[2,3-d]pyrimidin-4-amine

HRID 1443783Notes

Reaction equation

HRID 1443783 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(O)C.C(=O)([O-])[O-].C([N:21](C(C)C)CC)(C)C>C(#N)C>[N:5]1[C:4]2[S:8][CH:9]=[CH:10][C:3]=2[C:2]([NH2:21])=[N:7][CH:6]=1

Participants

7

Reactant 5

HCID 702EthanolHCID 19660Carbonate IonHCID 81531DiisopropylethylamineHCID 7366184-Chlorothieno[2,3-d]pyrimidineHCID 178435178HCID 178435178, compound

Product 1

HCID 4269486thieno[2,3-d]pyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

An amine (VIII) is added to a solution of the 4-chlorothieno[2,3-d]pyrimidine (VII) in either ethanol or a mixture of acetonitrile and a base (for example an alkaline carbonate or diisopropylethylamine) in a closable bottle. The bottle is closed with a polypropylene cap, and heated overnight in a conventional oven at a temperature comprised between 40° and 120° C., preferably between 60 and 85° C. After cooling, the solvent is removed under reduced pressure, and the residue is purified by flash chromatography to provide the final thieno[2,3-d]pyrimidin-4-ylamine (I).

Workup

  1. customcap
  2. temperatureheated overnight in a conventional oven at a temperature
  3. customcomprised between 40° and 120° C., preferably between 60 and 85° C
  4. temperatureAfter cooling
  5. customthe solvent is removed under reduced pressure
  6. customthe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-d4931da115324a31a67ccb56a1bffee0
Source dataset
uspto-grants-2010_02
Patent number
US07662814B2

Reaction notes

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