Hydrochloric Acid → Ethyl 2-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-ylpyrimidine-5-carboxylate

HRID 2079814Notes

Reaction equation

HRID 2079814 reaction equation
C(OC([N:8]1[CH2:12][CH:11]2[CH2:13][N:14]([C:16]3[N:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][N:17]=3)[CH2:15][CH:10]2[CH2:9]1)=O)(C)(C)C.Cl.O1CCOCC1>>[CH2:13]1[CH:11]2[CH2:12][NH:8][CH2:9][CH:10]2[CH2:15][N:14]1[C:16]1[N:21]=[CH:20][C:19]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:18][N:17]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 59367583ethyl 2-[5-(tert-butoxycarbonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]pyrimidine-5-carboxylate

Product 1

HCID 59367682Ethyl 2-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-ylpyrimidine-5-carboxylateYield 120.7%

Procedure

To ethyl 2-[5-(tert-butoxycarbonyl)hexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl]pyrimidine-5-carboxylate (0.345 g, 0.9 mmol) was added 4M HCl in dioxane (2 ml, 8 mmol). The mixture was stirred at r.t. for 1 h, then evaporated to dryness. The residue was dissolved in methanol, loaded onto a SCX-2 cartridge, washed with methanol (100 ml), then eluted with 2M ammonia in methanol to give the title compound (0.285 g, 100%). LCMS purity >95%, m/z 263 [M+H]+.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in methanol
  3. washwashed with methanol (100 ml)
  4. washeluted with 2M ammonia in methanol

Sources & evidence

ORD record
ord-9fb03f53612f46bb9ec08719d99247f1
Source dataset
uspto-grants-2011_04
Patent number
US07932246B2

Reaction notes

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