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2,6-Diaminopyridine → 2-(6-amino-pyridin-2-ylamino)-6-bromo-8-cyclopentyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 586497
Notes
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Reaction equation

HRID 586497 reaction equation
[Br:1][C:2]1[C:14](=[O:15])[N:13]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:5]2[N:6]=[C:7](S(C)=O)[N:8]=[CH:9][C:4]=2[C:3]=1[CH3:21].[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([NH2:29])[N:24]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:14](=[O:15])[N:13]([CH:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:5]2[N:6]=[C:7]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[N:8]=[CH:9][C:4]=2[C:3]=1[CH3:21].[NH2:22][C:23]1[N:24]=[C:25]([NH:29][C:7]2[N:8]=[CH:9][C:4]3[C:3]([CH3:21])=[C:2]([Br:1])[C:14](=[O:15])[N:13]([CH:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)[C:5]=3[N:6]=2)[CH:26]=[CH:27][CH:28]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 88612,6-DiaminopyridineHCID 113721276-bromo-8-cyclopentyl-5-methyl-2-(methylsulfinyl)pyrido[2,3-d]pyrimidin-7(8H)-one

Product 2

HCID 53302836-Bromo-8-cyclopentyl-5-methyl-2-(pyridin-2-ylamino)-8H-pyrido[2,3-d]pyrimidin-7-oneHCID 101269592-(6-amino-pyridin-2-ylamino)-6-bromo-8-cyclopentyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-oneYield 18.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-bromo-8-cyclopentyl-2-methanesulfinyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (370 mg, 1.0 mmol) and 2,6-diaminopyridine (163 mg, 1.5 mmol) in toluene (5 mL) was heated at 120° C. overnight. The solid formed upon cooling was collected by filtration, washed with toluene and sonicated in hot MeOH. After filtration the solid was dried further to give the desired product 2-(6-amino-pyridin-2-ylamino)-6-bromo-8-cyclopentyl-5-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (39 mg, 9.3%). mp: >274.6˜276° C. Calc'd for C18H19BrN6O. 0.2H2O: C, 51.61; H, 4.67; N, 20.06. Found: C, 51.42; H, 4.44; N, 19.87.

Workup

  1. customThe solid formed
  2. temperatureupon cooling
  3. filtrationwas collected by filtration
  4. washwashed with toluene
  5. customsonicated in hot MeOH
  6. filtrationAfter filtration the solid
  7. customwas dried further

Sources & evidence

ORD record
ord-491adeed9acc4e978101d1a8a8e4ecd8
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06936612B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes