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Sodium Methoxide → 1-(3-(azetidine-1-carbonyl)phenyl)-3-cyclopropyl-5-((2-fluoro-4-iodophenyl)amino)-6,8-dimethylpyrido[4,3-d]pyrimidine-2,4,7(1H,3H,6H)-trione

HRID 1487169
Notes
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Reaction equation

HRID 1487169 reaction equation
[N:1]1([C:5]([C:7]2[CH:8]=[C:9]([NH:13][C:14]3[C:23]4[C:22](=[O:24])[N:21]([CH:25]5[CH2:27][CH2:26]5)[C:20](=[O:28])[N:19]([C:29]5[CH:34]=[CH:33][C:32]([I:35])=[CH:31][C:30]=5[F:36])[C:18]=4[N:17]([CH3:37])[C:16](=[O:38])[C:15]=3[CH3:39])[CH:10]=[CH:11][CH:12]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1.C[O-].[Na+]>O1CCCC1>[N:1]1([C:5]([C:7]2[CH:8]=[C:9]([N:13]3[C:14]4=[C:15]([CH3:39])[C:16](=[O:38])[N:17]([CH3:37])[C:18]([NH:19][C:29]5[CH:34]=[CH:33][C:32]([I:35])=[CH:31][C:30]=5[F:36])=[C:23]4[C:22](=[O:24])[N:21]([CH:25]4[CH2:27][CH2:26]4)[C:20]3=[O:28])[CH:10]=[CH:11][CH:12]=2)=[O:6])[CH2:2][CH2:3][CH2:4]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 89816146HCID 89816146, compound

Product 1

HCID 717315841-(3-(azetidine-1-carbonyl)phenyl)-3-cyclopropyl-5-((2-fluoro-4-iodophenyl)amino)-6,8-dimethylpyrido[4,3-d]pyrimidine-2,4,7(1H,3H,6H)-trioneYield 82.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-((3-(azetidine-1-carbonyl)phenyl)amino)-3-cyclopropyl-1-(2-fluoro-4-iodophenyl)-6,8-dimethylpyrido[2,3-d]pyrimidine-2,4,7(1H,3H,8H)-trione (4b) (0.11 g, 0.17 mmol) was taken in tetrahydrofuran (3 ml) at room temperature, sodium methoxide (25% in MeOH, 371 mg, 1.71 mmol) was added and the reaction mixture was stirred at the same temperature for 1 hr under nitrogen atmosphere. The progress of the reaction was monitored by HPLC. After complete consumption of the substrate, the reaction mixture was diluted with HCl (2 mL, 2 N) and concentrated under vacuum. To the residue DCM (20 ml) was added, the organic layer was dried over sodium sulphate and concentrated under vacuum to give the crude compound which was purified by column chromatography to give the title product (0.09 g).

Workup

  1. customAfter complete consumption of the substrate
  2. additionthe reaction mixture was diluted with HCl (2 mL, 2 N)
  3. concentrationconcentrated under vacuum
  4. additionTo the residue DCM (20 ml) was added
  5. dry with materialthe organic layer was dried over sodium sulphate
  6. concentrationconcentrated under vacuum
  7. customto give the crude compound which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-9f53a17db25841918ac6765869384b21
Source dataset
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09428499B2

Reaction notes

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