Trifluoroacetic acid → Ethyl 3-hydroxy-8,8-dimethyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-2-carboxylate

HRID 346478Notes

Reaction equation

HRID 346478 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][CH2:17][C:18]([CH3:20])([CH3:19])[C:12]2=[N:11][C:10]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22])C1C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[OH:8][C:9]1[C:14](=[O:15])[N:13]2[CH2:16][CH2:17][C:18]([CH3:19])([CH3:20])[C:12]2=[N:11][C:10]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21080171Ethyl 3-(benzyloxy)-8,8-dimethyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-2-carboxylate

Product 1

HCID 54683255Ethyl 3-hydroxy-8,8-dimethyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-2-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Intermediate 4, ethyl 3-(benzyloxy)-8,8-dimethyl-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-2-carboxylate, (650 mg, 1.9 mmol) was treated with 6 mL trifluoroacetic acid (16 hrs) then concentrated in vacuo. The remaining residue was dissolved in CH2Cl2 and washed with H2O. Concentration of the CH2Cl2 layer gave 430 mg of a solid (Yield=90%) which could be further purified by trituration with diethyl ether. 1H NMR (300 MHz, CDCl3) δ ppm: 10.81 (1 H, s) 4.45 (2 H, q, J=7.0 Hz) 3.97–4.12(2 H, m) 1.95–2.15 (2 H, m) 1.41 (3 H, t, J=7.1 Hz) 1.33 (6 H, s); LC/MS m/z 253 (M+H).

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe remaining residue was dissolved in CH2Cl2
  3. washwashed with H2O

Sources & evidence

ORD record
ord-f5aa7f741e0d44a5aec5f5114601bbca
Source dataset
uspto-grants-2007_02
Patent number
US07173022B2

Reaction notes

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