Trifluoroacetic acid → HCID 136247224, compound

HRID 1022458Notes

Reaction equation

HRID 1022458 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]2[NH:15][C:16](=[O:31])[C:17]3[CH:22]=[CH:21][N:20]([CH2:23][O:24]CC[Si](C)(C)C)[C:18]=3[N:19]=2)[CH2:10][CH2:9]1.FC(F)(F)C(O)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:9][CH2:10][N:11]([C:14]2[NH:15][C:16](=[O:31])[C:17]3[CH:22]=[CH:21][N:20]([CH2:23][OH:24])[C:18]=3[N:19]=2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 136344414HCID 136344414, compound

Product 1

HCID 136247224HCID 136247224, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(4-(2-fluorophenyl)piperazin-1-yl)-7-((2-(trimethylsilyl)ethoxy)methyl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (30 mg, 67.6 μmol) in methylene chloride (3.38 mL) was treated dropwise with trifluoroacetic acid (1.13 mL). The reaction was stirred at room temperature for 2 h, and was then concentrated in vacuo onto Celite®. Flash chromatography (12 g silica gel column, 40-80% ethyl acetate/hexanes) afforded 2-[4-(2-fluoro-phenyl)-piperazin-1-yl]-7-hydroxymethyl-3,7-dihydro-pyrrolo[2,3-d]pyrimidin-4-one as a light grey solid (11.2 mg, 48.2%). 1H NMR (400 MHz, DMSO-d6) δ ppm 2.97-3.15 (m, 4H) 3.71 (d, J=5.08 Hz, 4H) 5.32 (d, J=7.42 Hz, 2H) 6.28 (d, J=3.52 Hz, 1H) 6.31-6.39 (m, 1H) 6.85 (d, J=3.52 Hz, 1H) 6.93-7.21 (m, 4H) 10.89 (s, 1H). LC-MS calcd. for C17H19FN5O2 [(M+H)+] 344, obsd. 344.1.

Workup

  1. concentrationwas then concentrated in vacuo onto Celite®

Sources & evidence

ORD record
ord-9a2cd4da25cc40cfa58b1214b6faaf20
Source dataset
uspto-grants-2014_05
Patent number
US08722661B2

Reaction notes

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