Hydrochloric Acid → HCID 86655329, compound

HRID 877005Notes

Reaction equation

HRID 877005 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([NH:9]C=O)=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])[N:15]=2)[N:3]=1.Cl.[OH-].[Na+]>C(O)C>[NH2:1][C:2]1[N:3]=[C:4]([NH:12][CH2:13][C:14]2[N:15]=[C:16]([N:20]3[CH2:24][CH2:23][CH2:22][C:21]3=[O:25])[CH:17]=[CH:18][CH:19]=2)[C:5]([NH2:9])=[C:6]([Cl:8])[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86655328HCID 86655328, compound

Product 1

HCID 86655329HCID 86655329, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of as N-(2-amino-4-chloro-6-{[6-(2-oxo-pyrrolidin-1-yl)pyridin-2-ylmethyl]amino}pyrimidin-5-yl)formamide (3.41 g, 9.43 mmol) in ethanol (36 mL) was treated with hydrochloric acid (6-M, 8 mL), heated at reflux for 2 h, cooled and the pH adjusted to 13 with aqueous sodium hydroxide (5-M). The mixture was extracted with EtOAc (×3) and the combined organic extracts were dried (Na2SO4) and concentrated in vacuo to give the title compound (2.12 g, 68%) as a coral pink solid; LC-MS retention time 1.64 min; (M+H)+ 334.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 h
  3. temperaturecooled
  4. extractionThe mixture was extracted with EtOAc (×3)
  5. dry with materialthe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3ab3b30f4a3a4b9394b054747f1b2eb2
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

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