5-((4-chlorophenyl)(hydroxy)methyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-6-(3-(trifluoromethoxy)phenoxy)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione → HCID 118863100, compound

HRID 63902Notes

Reaction equation

HRID 63902 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:43])[C:9]2[C:17]3[C:16](=[O:18])[N:15]([CH2:19][CH2:20][CH2:21][O:22]C4CCCCO4)[C:14](=[O:29])[N:13]([CH3:30])[C:12]=3[S:11][C:10]=2[O:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][C:39]([F:42])([F:41])[F:40])[CH:33]=2)=[CH:4][CH:3]=1>Cl.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:43])[C:9]2[C:17]3[C:16](=[O:18])[N:15]([CH2:19][CH2:20][CH2:21][OH:22])[C:14](=[O:29])[N:13]([CH3:30])[C:12]=3[S:11][C:10]=2[O:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([O:38][C:39]([F:41])([F:42])[F:40])[CH:33]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 1188631245-((4-chlorophenyl)(hydroxy)methyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-6-(3-(trifluoromethoxy)phenoxy)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 118863100HCID 118863100, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 5-((4-chlorophenyl)(hydroxy)methyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-6-(3-(trifluoromethoxy)phenoxy)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (30 mg, 0.047 mmol) in concentrated HCl (1 mL) and MeOH (5 mL) was stirred at RT for 1 h. The reaction was concentrated to a residue which was purified by Prep HPLC to give 5-((4-chlorophenyl) (hydroxy)methyl)-3-(3-hydroxypropyl)-1-methyl-6-(3-(trifluoromethoxy)phenoxy) thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (6 mg, 23.0% yield) as a white solid. 1H NMR (DMSO-d6) δ: 7.47 (t, J=8.3 Hz, 1H), 7.34 (d, J=8.5 Hz, 2H), 7.26 (d, J=8.5 Hz, 2H), 7.10 (dd, J=28.1, 8.2 Hz, 2H), 6.98 (s, 1H), 6.33 (d, J=7.7 Hz, 1H), 6.16 (d, J=7.6 Hz, 1H), 4.51 (t, J=5.2 Hz, 1H), 3.95 (s, 2H), 3.45 (d, J=5.4 Hz, 2H), 3.41 (s, 3H), 1.71 (s, 2H). LCMS: [M+-OH] 539 and TR=3.084 min.

Workup

  1. concentrationThe reaction was concentrated to a residue which
  2. customwas purified by Prep HPLC

Sources & evidence

ORD record
ord-7fca74308df94c508a4bb113a1b29abd
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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