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Potassium Carbonate → 3-Ethyl-5-[2-(6-methoxy-pyridin-3-ylamino)-pyrimidin-4-yl]-4-methyl-3H-thiazol-2-one

HRID 601445
Notes
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Reaction equation

HRID 601445 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[S:11][C:10](=[O:12])[N:9]([CH2:13][CH3:14])[C:8]=1[CH3:15])=O.[N+]([O-])(O)=O.[CH3:21][O:22][C:23]1[N:28]=[CH:27][C:26]([NH:29][C:30]([NH2:32])=[NH:31])=[CH:25][CH:24]=1.C([O-])([O-])=O.[K+].[K+]>COCCO>[CH2:13]([N:9]1[C:8]([CH3:15])=[C:7]([C:5]2[CH:4]=[CH:3][N:32]=[C:30]([NH:29][C:26]3[CH:27]=[N:28][C:23]([O:22][CH3:21])=[CH:24][CH:25]=3)[N:31]=2)[S:11][C:10]1=[O:12])[CH3:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 672738395-(3-Dimethylamino-acryloyl)-3-ethyl-4-methyl-3H-thiazol-2-oneHCID 1784923121-(6-Methoxypyridin-3-yl)guanidine nitrate

Product 1

HCID 114051633-Ethyl-5-[2-(6-methoxy-pyridin-3-ylamino)-pyrimidin-4-yl]-4-methyl-3H-thiazol-2-oneYield 39.4%

Reagents, catalysts & solvents 1

HCID 8019
2-Methoxyethanol
Solvent

Conditions

Temperature
120 °C

Procedure

5-(3-Dimethylamino-acryloyl)-3-ethyl-4-methyl-3H-thiazol-2-one (80 mg, 0.333 mmol), N-(6-methoxy-pyridin-3-yl)-guanidine nitrate (76 mg, 0.333 mmol) and K2CO3 (185 mg, 1.332 mmol) were combined in of 2-methoxyethanol (4 mL) and the mixture was heated at 120° C. for 22 h. After cooling, the inorganics were filtered off and the filtrate was concentrated to dryness. The crude product was purified by SiO2 gel chromatography. Pooling of the desired fractions afforded the title compound (45 mg, 39%). 13C-NMR (d6-DMSO) δ: 14.5, 14.7, 37.3, 53.7, 109.0, 110.3, 128.4, 131.82, 132.4, 137.8, 138.4, 152.7, 159.5, 160.3, 164.7, 170.1. Remaining analytical data in Table 2.

Workup

  1. temperatureAfter cooling
  2. filtrationthe inorganics were filtered off
  3. concentrationthe filtrate was concentrated to dryness
  4. customThe crude product was purified by SiO2 gel chromatography

Sources & evidence

ORD record
ord-9f436ab52e6a4ffbad7dcc65bfad9eb2
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07902361B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes