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Pentylamine → Methyl 4-((2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-fluorobenzoate

HRID 1617162
Notes
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Reaction equation

HRID 1617162 reaction equation
[CH2:1]([NH2:6])[CH2:2][CH2:3][CH2:4][CH3:5].[NH2:7][C:8]1[N:13]=[C:12](Cl)[C:11]([CH2:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=2[F:26])=[C:10]([CH3:27])[N:9]=1>O1CCOCC1>[NH2:7][C:8]1[N:9]=[C:10]([CH3:27])[C:11]([CH2:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=2[F:26])=[C:12]([NH:6][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[N:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 8060PentylamineHCID 86633399Methyl 4-((2-amino-4-chloro-6-methylpyrimidin-5-yl)methyl)-3-fluorobenzoate

Product 1

HCID 66819400Methyl 4-((2-amino-4-methyl-6-(pentylamino)pyrimidin-5-yl)methyl)-3-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Pentylamine (5.82 mL) was added to a solution of the product from step (iii) (3.1 g) in dioxane (50 mL). The resulting mixture was stirred at 100° C. for 50 h. The mixture was allowed to cool and then the solvent was evaporated under reduced pressure. The crude product was purified by flash silica chromatography eluting with 2 to 5% MeOH in DCM. to give the subtitle compound as a yellow solid 1.52 g.

Workup

  1. temperatureto cool
  2. customthe solvent was evaporated under reduced pressure
  3. customThe crude product was purified by flash silica chromatography
  4. washeluting with 2 to 5% MeOH in DCM

Sources & evidence

ORD record
ord-2657c1b39be64a65905797da88a505e0
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08765939B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes