Ammonium Chloride → 4-(4-Carbamoyl-2-ethoxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxamide

HRID 450529Notes

Reaction equation

HRID 450529 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:12]3[C:19]([CH3:20])=[C:18]([C:21]([O:23]C)=O)[S:17][C:13]=3[N:14]=[CH:15][N:16]=2)=[C:6]([O:25][CH2:26][CH3:27])[CH:5]=1)(=[O:3])[NH2:2].[Cl-].[NH4+:29]>N.CO>[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]2[C:12]3[C:19]([CH3:20])=[C:18]([C:21]([NH2:29])=[O:23])[S:17][C:13]=3[N:14]=[CH:15][N:16]=2)=[C:6]([O:25][CH2:26][CH3:27])[CH:5]=1)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 46182171Methyl 4-(4-carbamoyl-2-ethoxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 461826974-(4-Carbamoyl-2-ethoxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxamideYield 67.3%

Reagents, catalysts & solvents 1

HCID 21705897Ammonia methanolSolvent

Procedure

Methyl 4-(4-carbamoyl-2-ethoxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-carboxylate (0.025 g, 0.06 mmol) and ammonium chloride (0.250 g, 4.67 mmol) in 7N ammonia/MeOH (3.5 mL) were heated at 100° C. in a sealed-tube for 14 days. The solution was cooled and the residue filtered. The precipitate was washed with water to yield white solid (0.015 g, 63%).

Workup

  1. temperatureThe solution was cooled
  2. filtrationthe residue filtered
  3. washThe precipitate was washed with water

Sources & evidence

ORD record
ord-393d5a144d894b78b735d940efc80afa
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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