Trifluoroacetic acid → HCID 118863117, compound

HRID 63932Notes

Reaction equation

HRID 63932 reaction equation
[Cl:1][C:2]1[CH:46]=[CH:45][C:5]([CH2:6][C:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][O:20]C4CCCCO4)[C:12](=[O:27])[N:11]([CH2:28][CH2:29][CH2:30][O:31]C4CCCCO4)[C:10]=3[O:9][C:8]=2[C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=2)=[CH:4][CH:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]2[C:15]3[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][OH:20])[C:12](=[O:27])[N:11]([CH2:28][CH2:29][CH2:30][OH:31])[C:10]=3[O:9][C:8]=2[C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([Cl:44])[CH:39]=2)=[CH:45][CH:46]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 118863110HCID 118863110, compound

Product 1

HCID 118863117HCID 118863117, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-1,3-bis(3-(tetrahydro-2H-pyran-2-yl oxy) propyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione (67 mg, 0.1 mmol) in DCM (5 mL) was added TFA (1 mL). The reaction was stirred at RT for 1 h then concentrated to a residue which was diluted with EA (10 mL) and water (2 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-1,3-bis(3-hydroxypropyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione (29 mg, 58% yield) as an oil. 1H NMR (DMSO-d6) δ: 7.61 (s, 1H), 7.54 (d, J=7.7 Hz, 1H), 7.42 (t, J=7.9 Hz, 1H), 7.36 (d, J=8.2 Hz, 1H), 7.28 (s, 4H), 4.35 (s, 2H), 4.29 (t, J=6.9 Hz, 2H), 4.09 (t, J=7.1 Hz, 2H), 3.71 (t, J=5.9 Hz, 2H), 3.62 (t, J=6.3 Hz, 2H), 2.16-2.02 (m, 2H), 1.94-1.80 (m, 2H). LCMS: MH+ 503 and TR=2.826 min.

Workup

  1. concentrationthen concentrated to a residue which
  2. additionwas diluted with EA (10 mL) and water (2 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated to a residue which
  5. customwas purified by Prep HPLC

Sources & evidence

ORD record
ord-82d1f5f2ae4049c18b3de52b3835d4ee
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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