Pyridine → Ethyl{[4-(4-amino-6-ethylthieno[2,3-d]pyrimidin-5-yl)phenyl]amino}(oxo)acetate

HRID 227637Notes

Reaction equation

HRID 227637 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[S:10][C:9]=2[CH2:18][CH3:19])=[CH:4][CH:3]=1.Cl[C:21](=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].N1C=CC=CC=1>ClCCl>[CH2:25]([O:24][C:22](=[O:23])[C:21]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[S:10][C:9]=2[CH2:18][CH3:19])=[CH:6][CH:7]=1)=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 20884Ethoxalyl chlorideHCID 690614255-(4-Aminophenyl)-6-ethylthieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 69056684Ethyl{[4-(4-amino-6-ethylthieno[2,3-d]pyrimidin-5-yl)phenyl]amino}(oxo)acetateYield 64.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 78A (0.065 g, 0.25 mmol), ethyl chloro(oxo)acetate (0.028 mL, 0.25 mmol), and pyridine (0.02 mL, 0.25 mmol) in dichloromethane (5 mL) was stirred at room temperature overnight and partitioned between water and dichloromethane. The organic extract was washed with brine, dried (MgSO4), filtered, and concentrated. The concentrate was purified by silica gel column chromatography with 5% methanol/dichloromethane to provide 60 mg of the desired product. MS (ESI(+)) m/e 371(M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 1.15 (t, J=7.46 Hz, 3H); 1.34 (t, J=7.12 Hz, 3H); 2.64 (q, J=7.46 Hz, 2H); 4.34 (q, J=7.12 Hz, 2H); 7.41 (d, J=8.48 Hz, 2H); 7.93 (d, J=8.82 Hz, 2H); 8.27 (s, 1H); 11.00 (s, 1H).

Workup

  1. custompartitioned between water and dichloromethane
  2. extractionThe organic extract
  3. washwas washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by silica gel column chromatography with 5% methanol/dichloromethane

Sources & evidence

ORD record
ord-a4f3b1f49759457599e27723436b3943
Source dataset
uspto-grants-2009_07
Patent number
US07560552B2

Reaction notes

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