6-(3-chlorophenoxy)-1-methyl-2,4-dioxo-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carbaldehyde → HCID 118863106, compound

HRID 63887Notes

Reaction equation

HRID 63887 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[O:5][C:6]1[S:27][C:9]2[N:10]([CH3:26])[C:11](=[O:25])[N:12]([CH2:15][CH2:16][CH2:17][O:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[C:13](=[O:14])[C:8]=2[C:7]=1[CH:28]=[O:29].[Cl:33][C:34]1[CH:35]=[C:36]([Mg]Br)[CH:37]=[CH:38][CH:39]=1>C1COCC1.CC(=O)OCC.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[O:5][C:6]1[S:27][C:9]2[N:10]([CH3:26])[C:11](=[O:25])[N:12]([CH2:15][CH2:16][CH2:17][O:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][O:20]3)[C:13](=[O:14])[C:8]=2[C:7]=1[CH:28]([C:37]1[CH:36]=[CH:35][C:34]([Cl:33])=[CH:39][CH:38]=1)[OH:29]

Participants

6

Reactant 2

HCID 1188631296-(3-chlorophenoxy)-1-methyl-2,4-dioxo-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carbaldehydeHCID 178478127HCID 178478127, compound

Product 1

HCID 118863106HCID 118863106, compoundYield 56.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(3-chlorophenoxy)-1-methyl-2,4-dioxo-3-(3-(tetrahydro-2H-pyran-2-yloxy) propyl)-1,2,3,4-tetrahydrothieno[2,3-d]pyrimidine-5-carbaldehyde (65 mg, 0.136 mmol) in THF (2 mL) was added (3-chlorophenyl)magnesium bromide (35 mg, 0.163 mmol). The reaction was stirred at RT for 15 minutes then diluted with EA (20 mL) and water (20 mL). The organic layer was dried over Na2SO4 and concentrated to give a residue which was purified by chromatography eluted with PE/EA (4:1) to give 6-(3-chlorophenoxy)-5-((4-chlorophenyl) (hydroxy)methyl)-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (45 mg, 56.3% yield) as a yellow oil. LCMS: MH+ 591 and TR=2.138 min.

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. concentrationconcentrated
  3. customto give a residue which
  4. customwas purified by chromatography
  5. washeluted with PE/EA (4:1)

Sources & evidence

ORD record
ord-07a51f06d72e40908d1dc621d8cdf160
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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