5-(4-chlorobenzyl)-6-(3-chlorophenyl)-3-(3-(tetrahydro-2H-pyran-2-yloxy) propyl)-1-((2-(trimethylsilyl)ethoxy)methyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione → 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-3-(3-hydroxypropyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 63929Notes

Reaction equation

HRID 63929 reaction equation
[Cl:1][C:2]1[CH:44]=[CH:43][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](COCC[Si](C)(C)C)[C:10]=3[O:9][C:8]=2[C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=2)=[CH:4][CH:3]=1>C(Cl)Cl.C(O)(C(F)(F)F)=O.O>[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])[NH:11][C:10]=3[O:9][C:8]=2[C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=2)=[CH:43][CH:44]=1

Participants

5

Reactant 1

HCID 1317372145-(4-chlorobenzyl)-6-(3-chlorophenyl)-3-(3-(tetrahydro-2H-pyran-2-yloxy) propyl)-1-((2-(trimethylsilyl)ethoxy)methyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 1188631415-(4-chlorobenzyl)-6-(3-chlorophenyl)-3-(3-hydroxypropyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 23%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-3-(3-(tetrahydro-2H-pyran-2-yloxy) propyl)-1-((2-(trimethylsilyl)ethoxy)methyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione (20 mg, 0.03 mmol) in DCM (0.8 mL) was added in TFA (0.8 mL). The reaction was stirred at RT for 2 h then diluted with DCM (5 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)-3-(3-hydroxypropyl)furo[2,3-d]pyrimidine-2,4(1H,3H)-dione (3 mg, 23% yield) as an oil. 1H NMR (DMSO-d6) δ: 7.43 (d, J=3.4 Hz, 3H), 7.34 (d, J=8.4 Hz, 3H), 7.26 (d, J=8.4 Hz, 2H), 4.53 (s, 1H), 4.28 (s, 2H), 3.85 (t, J=7.1 Hz, 2H), 3.40 (s, 2H), 1.71-1.58 (m, 2H). LCMS: MH+ 445 and TR=2.803 min.

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. concentrationconcentrated to a residue which
  3. customwas purified by Prep HPLC

Sources & evidence

ORD record
ord-fe7eb0ca8fd548ebb6f3b6def14ceeac
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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