5-(1-hydroxy-3-methylbutyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy) propyl)-6-(3-(trifluoromethoxy)phenyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione → 5-(1-hydroxy-3-methylbutyl)-3-(3-hydroxypropyl)-1-methyl-6-(3-(trifluoromethoxy)phenyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 63906Notes

Reaction equation

HRID 63906 reaction equation
[OH:1][CH:2]([C:7]1[C:15]2[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][O:20]C3CCCCO3)[C:12](=[O:27])[N:11]([CH3:28])[C:10]=2[S:9][C:8]=1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][C:36]([F:39])([F:38])[F:37])[CH:30]=1)[CH2:3][CH:4]([CH3:6])[CH3:5]>Cl.CO>[OH:1][CH:2]([C:7]1[C:15]2[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19][OH:20])[C:12](=[O:27])[N:11]([CH3:28])[C:10]=2[S:9][C:8]=1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][C:36]([F:37])([F:38])[F:39])[CH:30]=1)[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

4

Reactant 1

HCID 1188631145-(1-hydroxy-3-methylbutyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy) propyl)-6-(3-(trifluoromethoxy)phenyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 1188630965-(1-hydroxy-3-methylbutyl)-3-(3-hydroxypropyl)-1-methyl-6-(3-(trifluoromethoxy)phenyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 47.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 5-(1-hydroxy-3-methylbutyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-6-(3-(trifluoromethoxy)phenyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (15 mg, 0.026 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-(1-hydroxy-3-methylbutyl)-3-(3-hydroxypropyl)-1-methyl-6-(3-(trifluoromethoxy)phenyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (6 mg, 46.9% yield) as a white solid. 1H NMR (CDCl3) δ: 7.49 (t, J=8.0 Hz, 1H), 7.35 (d, J=7.7 Hz, 1H), 7.29 (d, J=8.4 Hz, 1H), 5.39 (d, J=11.9 Hz, 1H), 4.85-4.65 (m, 1H), 4.26 (t, J=6.1 Hz, 2H), 3.70-3.49 (m, 5H), 2.89 (s, 1H), 2.06-1.89 (m, 3H), 1.76 (dt, J=13.4, 6.6 Hz, 1H), 1.43-1.33 (m, 1H), 0.80 (dd, J=9.3 and 6.7 Hz, 6H). LCMS: MH+ 487 and TR=2.971 min.

Workup

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

Sources & evidence

ORD record
ord-18b5e283ac6b4af59245343ae0e38f92
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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