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p-Toluenesulfonic acid → methyl 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,2-dimethyl-3H-benzofuran-4-carboxylate

HRID 2364682
Notes
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Reaction equation

HRID 2364682 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:13]([O:15][CH3:16])=[O:14])=[C:6]2[C:10]=1[O:9][C:8]([CH3:12])([CH3:11])[CH2:7]2.Cl[C:18]1[N:27]=[CH:26][C:25]2[N:24]([CH3:28])[C:23](=[O:29])[C@@H:22]([CH2:30][CH3:31])[N:21]([CH:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[C:20]=2[N:19]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CC(O)CC(C)C>[CH:32]1([N:21]2[C:20]3[N:19]=[C:18]([NH:1][C:2]4[CH:3]=[CH:4][C:5]([C:13]([O:15][CH3:16])=[O:14])=[C:6]5[C:10]=4[O:9][C:8]([CH3:12])([CH3:11])[CH2:7]5)[N:27]=[CH:26][C:25]=3[N:24]([CH3:28])[C:23](=[O:29])[C@H:22]2[CH2:30][CH3:31])[CH2:33][CH2:34][CH2:35][CH2:36]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 24820413(R)-2-Chloro-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-oneHCID 68107595Methyl 7-amino-2,2-dimethyl-2,3-dihydrobenzofuran-4-carboxylate

Product 1

HCID 68107267methyl 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,2-dimethyl-3H-benzofuran-4-carboxylate
Yield 106.7%

Reagents, catalysts & solvents 1

HCID 79104-Methyl-2-PentanolSolvent

Procedure

Methyl 7-amino-2,2-dimethyl-3H-benzofuran-4-carboxylate 4d (770 mg, 3.48 mmol) was dissolved in 20 mL of 1,3-dimethyl-butanol followed by the addition of (7R)-2-chloro-8-cyclopentyl-7-ethyl-5-methyl-5H-pteridin-6-one 1o (1.23 g, 4.18 mmol) and p-toluenesulfonic acid (1.06 g, 5.57 mmol) successively. The reaction solution was heated to reflux for 2 hours with stirring. The resulting solution was added with 50 mL of saturated sodium bicarbonate solution, extracted with ethyl acetate (50 mL×3). The combined organic phase was washed with water (30 mL), saturated sodium chloride solution (20 mL) successively and dried over anhydrous magnesium sulfate. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound methyl 7-[[(7R)-8-cyclopentyl-7-ethyl-5-methyl-6-oxo-7H-pteridin-2-yl]amino]-2,2-dimethyl-3H-benzofuran-4-carboxylate 4e (1.78 g, yield: 100%) as a light yellow solid.

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux for 2 hours
  3. extractionextracted with ethyl acetate (50 mL×3)
  4. washThe combined organic phase was washed with water (30 mL), saturated sodium chloride solution (20 mL) successively
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-01152de87ca1492d95c25142be2a67b7
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08691822B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes