Diisopropylethylamine → HCID 70981487, compound

HRID 2280783Notes

Reaction equation

HRID 2280783 reaction equation
[Br:1][C:2]1[C:3]([S:9][CH3:10])=[N:4][C:5](Cl)=[N:6][CH:7]=1.Cl.[CH3:12][C:13]1([NH2:16])[CH2:15][CH2:14]1.CCN(C(C)C)C(C)C>C(O)C>[Br:1][C:2]1[C:3]([S:9][CH3:10])=[N:4][C:5]([NH:16][C:13]2([CH3:12])[CH2:15][CH2:14]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 122647965-Bromo-2-chloro-4-(methylthio)pyrimidineHCID 12953687(1-Methylcyclopropyl)amine hydrochloride

Product 1

HCID 70981487HCID 70981487, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

To a stirring suspension of 5-bromo-2-chloro-4-(methylthio)pyrimidine (1.0 g, 4.18 mmol) in ethanol (6.0 mL) was added 1-methylcyclopropanamine hydrochloride (0.674 g, 6.26 mmol) and DIEA (2.188 mL, 12.53 mmol). The mixture was stirred at 90° C. for 16 h. Upon completion of the reaction as indicated by LCMS and TLC the reaction mixture was concentrated and purified by silica gel chromatography using a gradient of 0%-20% ethyl acetate in hexanes. The product fractions were combined and concentrated to afford 5-bromo-N-(1-methylcyclopropyl)-4-(methylthio)pyrimidin-2-amine (0.665 g, 58% yield) as a white solid. MS (ESI) m/z 276.2 [M+1]+.

Workup

  1. customUpon completion of the reaction
  2. concentrationwas concentrated
  3. custompurified by silica gel chromatography
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4514f7ed26f940b59a47c15786f5f9a7
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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