Hydrochloric Acid → HCID 86655316, compound

HRID 876963Notes

Reaction equation

HRID 876963 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]([CH2:20][O:21][C@H:22]3[CH2:26][CH2:25][O:24][CH2:23]3)[N:15]=2)[N:3]=1.Cl.[OH-].[Na+]>CCO>[Cl:8][C:6]1[N:7]=[C:2]([NH2:1])[N:3]=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][O:21][C@H:22]3[CH2:26][CH2:25][O:24][CH2:23]3)[N:15]=2)[C:5]=1[NH2:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86655315HCID 86655315, compound

Product 1

HCID 86655316HCID 86655316, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-[2-amino-4-chloro-6-({6-[(S)-(tetrahydrofuran-3-yl)oxymethyl]pyridin-2-ylmethyl}-amino)pyrimidin-5-yl]formamide (10.00 g, 26.40 mmol) and hydrochloric acid (6 M, 22 mL) in EtOH (100 mL) was heated at reflux for 15 h, cooled, basified with aqueous sodium hydroxide (5-M, 50 mL) and concentrated in vacuo to remove the EtOH. The resulting mixture was extracted with dichloromethane (×2) and the combined organic extracts were washed with saturated brine, dried (Na2SO4) and concentrated in vacuo to give the title compound (8.09 g, 87%) as a pink solid; LC-MS retention time 1.52 min; (M+H)+ 351.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 15 h
  3. temperaturecooled
  4. concentrationconcentrated in vacuo
  5. customto remove the EtOH
  6. extractionThe resulting mixture was extracted with dichloromethane (×2)
  7. washthe combined organic extracts were washed with saturated brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-54c554c6e8834140b6e6271dd549ca16
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

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