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Ethyl Acetoacetate → Ethyl 2-(2-acetylaminothiazol-4-yl)-4-(2-chloro-4-fluorophenyl)-6-methyl-1,4-dihydro-pyrimidin-5-carboxylate

HRID 1919563
Notes
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Reaction equation

HRID 1919563 reaction equation
Cl.[C:2]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11]([NH2:13])=[NH:12])[N:10]=1)(=[O:4])[CH3:3].[Cl:14][C:15]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:16]=1[CH:17]=O.[C:24]([O:30][CH2:31][CH3:32])(=[O:29])[CH2:25][C:26]([CH3:28])=O.C([O-])(=O)C.[Na+]>C(O)C>[C:2]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11]2[NH:13][C:26]([CH3:28])=[C:25]([C:24]([O:30][CH2:31][CH3:32])=[O:29])[CH:17]([C:16]3[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:15]=3[Cl:14])[N:12]=2)[N:10]=1)(=[O:4])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8868Ethyl AcetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 517045Sodium AcetateHCID 86640675HCID 86640675, compound

Product 1

HCID 59272704Ethyl 2-(2-acetylaminothiazol-4-yl)-4-(2-chloro-4-fluorophenyl)-6-methyl-1,4-dihydro-pyrimidin-5-carboxylateYield 35.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2 mmol 2-Acetylamino-4-thiazolformamidine hydrochloride, 2 mmol 2-chloro-4-fluorobenzaldehyde, 2 mmol ethyl acetoacetate and 2.2 mmol sodium acetate were reacted under reflux in 10 ml anhydrous ethanol for 20 hr, concentrated, and then ethyl acetate and water were added to separate the layers. The ethyl acetate layer was dried over anhydrous sodium sulfate, and separated by a column chromatography to obtain 0.31 g of a colorless crystal with mp 220-223° C.; 1H-NMR (400 MHz, DMSO-d6) δ 1.01-1.04 (3H, m); 2.13 (3H, s); 2.40-2.42 (3H, d); 3.91-3.97 (2H, m); 5.97 (1H, s); 7.15-7.39 (3H, m); 7.64-7.83 (1H, d); 8.33-8.98 (1H, d); 12.33 (1H, s); MS (EI) 436.0 (M+).

Workup

  1. concentrationconcentrated
  2. additionethyl acetate and water were added
  3. customto separate the layers
  4. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  5. customseparated by a column chromatography

Sources & evidence

ORD record
ord-d0988d1ef4624a47b9d4f3ff50068110
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08168642B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes