N,N-Dimethylaniline → (4-Chloro-5-phenylthieno[2,3-d]pyrimidin-2-yl)acetic acid ethyl ester

HRID 910191Notes

Reaction equation

HRID 910191 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[NH:7][C:8](=O)[C:9]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][S:12][C:10]=2[N:11]=1)[CH3:2].P(Cl)(Cl)([Cl:25])=O.CN(C)C1C=CC=CC=1>ClCCl>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[N:7]=[C:8]([Cl:25])[C:9]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][S:12][C:10]=2[N:11]=1)[CH3:2]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 13591037(4-Oxo-5-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)acetic acid ethyl ester

Product 1

HCID 11595162(4-Chloro-5-phenylthieno[2,3-d]pyrimidin-2-yl)acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of (4-oxo-5-phenyl-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)acetic acid ethyl ester (1.0 g, 3.185 mmol), phosphoryl chloride (15 ml) and N,N-dimethylaniline (4.8 ml) was heated under reflux for 6 hours and then left to stand at ambient temperature for 18 hours. The excess phosphoryl chloride was removed in vacuo to give a dark residue, which was dissolved in dichloromethane (100 ml) and then washed with water (2×50 ml) followed by saturated sodium hydrogen carbonate solution (50 ml). The organic layer was dried (MgSO4) and the solvent was removed in vacuo to give the crude product. Purification by flash chromatography (silica) eluting with dichloromethane and 40°-60° petroleum ether (3:1) gave (4-chloro-5-phenylthieno[2,3-d]pyrimidin-2-yl)acetic acid ethyl ester as a pale-yellow solid (0.86 g).

Workup

  1. temperatureunder reflux for 6 hours
  2. waitleft
  3. customThe excess phosphoryl chloride was removed in vacuo
  4. customto give a dark residue, which
  5. washwashed with water (2×50 ml)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvent was removed in vacuo
  8. customto give the crude product
  9. customPurification by flash chromatography (silica)
  10. washeluting with dichloromethane and 40°-60° petroleum ether (3:1)

Sources & evidence

ORD record
ord-a88a187d7b154a39b2b27c95d08576ce
Source dataset
uspto-grants-2011_09
Patent number
US08022076B2

Reaction notes

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