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Ethanol → (5-Phenyl-4-[(pyridin-2-ylmethyl)amino]thieno[2,3-d]pyrimidin-2-yl}acetic acid ethyl ester

HRID 910192
Notes
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Reaction equation

HRID 910192 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[N:7]=[C:8](Cl)[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].[NH2:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=1.C(N(CC)CC)C.C(O)C>O>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[N:7]=[C:8]([NH:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=2)[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 195092-PyridinemethanamineHCID 11595162(4-Chloro-5-phenylthieno[2,3-d]pyrimidin-2-yl)acetic acid ethyl ester

Product 1

HCID 11711155(5-Phenyl-4-[(pyridin-2-ylmethyl)amino]thieno[2,3-d]pyrimidin-2-yl}acetic acid ethyl esterYield 93.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of (4-chloro-5-phenylthieno[2,3-d]pyrimidin-2-yl)acetic acid ethyl ester (0.36 g, 1.08 mmol), 2-aminomethylpyridine (0.12 ml, 1.19 mmol), triethylamine (0.17 ml, 1.19 mmol) and ethanol (8 ml) was heated under reflux for 4 hours. The solution was then cooled to ambient temperature, poured into water (100 ml) and extracted with dichloromethane (3×50 ml). The combined organic extracts were dried (MgSO4) and the solvent removed in vacuo to give the crude product. Purification by flash chromatography (silica) eluting with ethyl acetate and 40°-60° petroleum ether (1:2) gave {5-phenyl-4-[(pyridin-2-ylmethyl)amino]thieno[2,3-d]pyrimidin-2-yl}acetic acid ethyl ester as a colourless gum (0.41 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hours
  3. extractionextracted with dichloromethane (3×50 ml)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customto give the crude product
  7. customPurification by flash chromatography (silica)
  8. washeluting with ethyl acetate and 40°-60° petroleum ether (1:2)

Sources & evidence

ORD record
ord-2658c3cb6abf45d69be7b67a60c37ef6
Source dataset
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08022076B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes