Hydrochloric Acid → HCID 67007470, compound

HRID 563864Notes

Reaction equation

HRID 563864 reaction equation
[CH3:1][N:2]1[CH2:24][CH2:23][C:5]2[N:6]=[C:7]([N:10]3[CH2:14][CH2:13][C@@H:12]([NH:15]C(=O)OC(C)(C)C)[CH2:11]3)[N:8]=[CH:9][C:4]=2[CH2:3]1.[ClH:25]>CO.O1CCOCC1>[ClH:25].[ClH:25].[ClH:25].[CH3:1][N:2]1[CH2:24][CH2:23][C:5]2[N:6]=[C:7]([N:10]3[CH2:14][CH2:13][C@@H:12]([NH2:15])[CH2:11]3)[N:8]=[CH:9][C:4]=2[CH2:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57833087HCID 57833087, compound

Product 1

HCID 67007470HCID 67007470, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl [(3R)-1-(6-methyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-yl)pyrrolidin-3-yl]carbamate (10.0 g, 30.0 mmol) was dissolved in methanol (40 mL) and cooled to 0° C. To this was added a solution of 4 N hydrochloric acid in dioxane (80 mL). The mixture was allowed to warm to room temperature and then stirred at room temperature for 1 hour and then evaporated to dryness. The residue was boiled with ethanol (100 mL) then cooled to 0° C. and the resulting precipitate was filtered off. This gave the title compound (6.99 g, yield 69%) as a pale pink hygroscopic solid. LCMS (ES+) M+H 234. 1H NMR (DMSO-d6) 2.12 (m, 1H) 2.30 (m, 1H) 2.86-2.94 (s+m, 4H) 3.14-3.24 (m, 1H) 3.37-3.46 (m, 1H) 3.56-3.77 (br m, 6H) 3.78 (br m, 1H) 4.13 (dd, J=14.6, 8.3 Hz, 1H) 4.35 (d, J=14.0 Hz, 1H) 8.28 (s, 1H) 8.52 (br s, 3H) 11.71 (br s, 1H). LRMS M+H 234.

Workup

  1. temperatureto warm to room temperature
  2. customevaporated to dryness
  3. temperaturethen cooled to 0° C.
  4. filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-3c9e9b6f8fa7472084416d8b2d22a310
Source dataset
uspto-grants-2011_11
Patent number
US08067589B2

Reaction notes

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