Hydrochloric Acid → HCID 178433154, compound

HRID 575529Notes

Reaction equation

HRID 575529 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][CH2:11]2)=[C:6]([OH:23])[N:5]=[C:4]([CH3:24])[N:3]=1.CC(O)C.[ClH:29]>C1COCC1>[ClH:29].[ClH:29].[NH2:1][C:2]1[N:3]=[C:4]([CH3:24])[N:5]=[C:6]([OH:23])[C:7]=1[CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 178433155HCID 178433155, compound

Product 1

HCID 178433154HCID 178433154, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Combine tert-butyl 4-[2-(4-amino-6-hydroxy-2-methyl-pyrimidin-5-yl)ethyl]piperidine-1-carboxylate (3.73 kg, 11.09 mol) and IPA in a 50 L reactor under a nitrogen atmosphere. Add 12 N hydrochloric acid (3.05 L, 36.6 mol) with stiffing over 3 h. Heat the mixture at 50° C. for 16 h, forming a thick slurry. At that time NMR analysis shows no BOC group remaining. Cool the reaction mixture to 20-25° C., diluting with THF (12 L). Collect the solids by filtration. The filtration is slow and may take over 24 h to complete. Wash with IPA (2×10 L). Dry the material in a vacuum oven at 50° C. to provide the title compound (3.117 kg, 91%).

Workup

  1. customforming a thick slurry
  2. temperatureCool the reaction mixture to 20-25° C.
  3. customCollect the solids
  4. filtrationby filtration
  5. filtrationThe filtration
  6. waitmay take over 24 h
  7. washWash with IPA (2×10 L)
  8. customDry the material in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-3b757a87d0aa4ddcb18eb331027bc475
Source dataset
uspto-grants-2015_05
Patent number
US09035051B1

Reaction notes

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