1-methyl-5-(3-methylbutanoyl)-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-6-(3-(trifluoromethoxy)phenyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione → HCID 118863142, compound

HRID 63899Notes

Reaction equation

HRID 63899 reaction equation
[CH3:1][N:2]1[C:7]2[S:8][C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:27])([F:26])[F:25])[CH:18]=3)=[C:10]([C:11](=[O:16])[CH2:12][CH:13]([CH3:15])[CH3:14])[C:6]=2[C:5](=[O:28])[N:4]([CH2:29][CH2:30][CH2:31][O:32]C2CCCCO2)[C:3]1=[O:39]>Cl.CO>[OH:32][CH2:31][CH2:30][CH2:29][N:4]1[C:5](=[O:28])[C:6]2[C:10]([C:11](=[O:16])[CH2:12][CH:13]([CH3:15])[CH3:14])=[C:9]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:23][C:24]([F:26])([F:25])[F:27])[CH:18]=3)[S:8][C:7]=2[N:2]([CH3:1])[C:3]1=[O:39]

Participants

4

Reactant 1

HCID 1188631451-methyl-5-(3-methylbutanoyl)-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 118863142HCID 118863142, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 1-methyl-5-(3-methylbutanoyl)-3-(3-((tetrahydro-2H-pyran-2-yl)oxy)propyl)-6-(3-(trifluoromethoxy)phenyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (30 mg, 0.053 mmol) in concentrated HCl (1 mL) and MeOH (5 mL) was stirred at RT for 1 h then concentrated to a residue which was purified by Prep HPLC to give 3-(3-hydroxypropyl)-1-methyl-5-(3-methylbutanoyl)-6-(3-(trifluoromethoxy)phenyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (6 mg, 23.4% yield) as a white solid. 1H NMR (CDCl3) δ: 7.48-7.37 (m, 2H), 7.32 (s, 1H), 7.26-7.23 (m, 1H), 4.18 (t, J=6.1 Hz, 2H), 3.61 (s, 3H), 3.55 (dd, J=11.7, 6.3 Hz, 2H), 3.04 (t, J=7.0 Hz, 1H), 2.54 (d, J=6.6 Hz, 2H), 2.14 (dt, J=13.3, 6.7 Hz, 1H), 1.97-1.85 (m, 2H), 0.84 (d, J=6.7 Hz, 7H). LCMS: MH+ 485 and TR=3.100 min.

Workup

  1. concentrationthen concentrated to a residue which
  2. customwas purified by Prep HPLC

Sources & evidence

ORD record
ord-3a280e8ff685476c9ab354257234d9e8
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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