Methyl 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylate → HCID 67381887, compound

HRID 532281Notes

Reaction equation

HRID 532281 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:14][C:8]2[N:9]=[CH:10][N:11]=[C:12]([Cl:13])[C:7]=2[C:6]=1[CH3:15])=[O:4].[NH2:16][C:17]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][C:18]=1[O:19][CH:20]([CH3:31])[CH2:21][CH2:22][NH:23]C(=O)OC(C)(C)C>O1CCOCC1>[ClH:13].[NH2:23][CH2:22][CH2:21][CH:20]([O:19][C:18]1[CH:32]=[C:33]([F:36])[CH:34]=[CH:35][C:17]=1[NH:16][C:12]1[C:7]2[C:6]([CH3:15])=[C:5]([C:3]([O:2][CH3:1])=[O:4])[S:14][C:8]=2[N:9]=[CH:10][N:11]=1)[CH3:31]

Participants

4

Reactant 2

HCID 2759834Methyl 4-chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylateHCID 58413342HCID 58413342, compound

Product 1

HCID 67381887HCID 67381887, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Chloro-5-methyl-thieno[2,3-d]pyrimidine-6-carboxylic acid methyl ester (1.25 g), tert-butyl 3-(2-amino-5-fluorophenoxy)butylcarbamate (1.7 g) and p-toloulsulfonic acid (175 mg) was dissolved in dioxane (30 ml) and the solution was heated under reflux overnight. Then the reaction mixture was concentrated in vacuo. The residue was treated with trifluoracetic acid 25% in dichloromethane and stirred at room temperature for 1 h. The solution was concentrated in vacuo and the residue was dissolved in dichloromethane and washed with sodium bicarbonate. The organic phase was separated, dried and concentrated in vacuo. The residue was triturated with Et2O and the precipitate was filtered.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux overnight
  3. concentrationThen the reaction mixture was concentrated in vacuo
  4. additionThe residue was treated with trifluoracetic acid 25% in dichloromethane
  5. concentrationThe solution was concentrated in vacuo
  6. dissolutionthe residue was dissolved in dichloromethane
  7. washwashed with sodium bicarbonate
  8. customThe organic phase was separated
  9. customdried
  10. concentrationconcentrated in vacuo
  11. customThe residue was triturated with Et2O
  12. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-b20aa250df104b6f925b894ca3b1c07d
Source dataset
uspto-grants-2014_10
Patent number
US08853193B2

Reaction notes

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