Ethanol → HCID 44220506, compound

HRID 237385Notes

Reaction equation

HRID 237385 reaction equation
[OH-].[Na+].C([O:5][C:6]([C:8]1[S:33][C:11]2[N:12]=[C:13]([NH2:32])[N:14]=[C:15]([C:16]3[CH:21]=[C:20]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C:19]([Cl:30])=[CH:18][C:17]=3[Cl:31])[C:10]=2[CH:9]=1)=[O:7])C.C(O)C>O>[NH2:32][C:13]1[N:14]=[C:15]([C:16]2[CH:21]=[C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:19]([Cl:30])=[CH:18][C:17]=2[Cl:31])[C:10]2[CH:9]=[C:8]([C:6]([OH:7])=[O:5])[S:33][C:11]=2[N:12]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 44220100HCID 44220100, compound

Product 1

HCID 44220506HCID 44220506, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium hydroxide (0.190 g; 4.75 mmol) was added to 2-Amino-4-(5-benzyloxy-2,4-dichloro-phenyl)-thieno[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (step 4 example 235). Ethanol (25 ml) was added followed by water (2.5 ml) and the reaction mixture was heated to reflux for 1 hour. The reaction mixture was allowed to cool and solvents were removed in vacuo. The resulting residue was dissolved in water and stirred in ice-water bath and the neutralised by the drop-wise addition of 37% (aq) hydrochloric acid solution. The reaction mixture was freeze dried to afford product as a yellow powder (containing 2 equivalents of NaCl) 1.33 g; 100%.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperatureto cool
  4. customsolvents were removed in vacuo
  5. dissolutionThe resulting residue was dissolved in water
  6. additionthe neutralised by the drop-wise addition of 37% (aq) hydrochloric acid solution
  7. customdried

Sources & evidence

ORD record
ord-50f9dcb267b744659b3a3dc48f5d13a0
Source dataset
uspto-grants-2014_02
Patent number
US08642594B2

Reaction notes

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