HCID 118863133, compound → HCID 118863140, compound

HRID 63894Notes

Reaction equation

HRID 63894 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[S:29][C:11]3[N:12]([CH3:28])[C:13](=[O:27])[N:14]([CH2:17][CH2:18][CH2:19][O:20]C4CCCCO4)[C:15](=[O:16])[C:10]=3[C:9]=2[CH:30]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)[OH:31])[CH:5]=[CH:6][CH:7]=1>Cl.CO>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[S:29][C:11]3[N:12]([CH3:28])[C:13](=[O:27])[N:14]([CH2:17][CH2:18][CH2:19][OH:20])[C:15](=[O:16])[C:10]=3[C:9]=2[CH:30]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)[OH:31])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 118863133HCID 118863133, compound

Product 1

HCID 118863140HCID 118863140, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 21893726Hydrochloride methanolSolvent

Procedure

A solution of 6-(3-chlorophenyl)-5-((4-chlorophenyl)(hydroxy)methyl)-1-methyl-3-(3-((tetra hydro-2H-pyran-2-yl)oxy)propyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (30 mg, 0.052 mmol) in 2N HCl/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 6-(3-chlorophenyl)-5-((4-chlorophenyl) (hydroxy)methyl)-3-(3-hydroxypropyl)-1-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (12 mg, 46.8% yield) as a white solid. 1H NMR (DMSO-d6) δ: 7.53-7.36 (m, 3H), 7.29 (t, J=7.2 Hz, 3H), 7.19 (d, J=8.4 Hz, 2H), 6.32 (d, J=9.1 Hz, 1H), 6.14 (d, J=9.0 Hz, 1H), 4.47 (t, J=5.2 Hz, 1H), 3.92 (t, J=7.3 Hz, 2H), 3.51 (s, 3H), 3.42 (dd, J=11.6, 6.2 Hz, 2H), 1.68 (d, J=6.4 Hz, 2H). LCMS: [M+-OH] 473 and TR=3.107 min.

Workup

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

Sources & evidence

ORD record
ord-bc323d710da642fe816fbf2bb590e2f2
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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