Cesium carbonate → 6-(4-chlorophenyl)-3-{3-methoxy-4-[(1-methyl-3-piperidinyl)methoxy]phenyl}thieno[3,2-d]pyrimidin-4(3H)-one

HRID 1181367Notes

Reaction equation

HRID 1181367 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([C:18]4[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([O:25][CH3:26])[CH:19]=4)[CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.Cl[CH2:28][CH:29]1[CH2:34][CH2:33][CH2:32][N:31]([CH3:35])[CH2:30]1.C([O-])([O-])=O.[Cs+].[Cs+]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH2:28][CH:29]5[CH2:34][CH2:33][CH2:32][N:31]([CH3:35])[CH2:30]5)=[C:20]([O:25][CH3:26])[CH:19]=4)[CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 1036743-(Chloromethyl)-1-methylpiperidineHCID 589808956-(4-chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-one

Product 1

HCID 589808356-(4-chlorophenyl)-3-{3-methoxy-4-[(1-methyl-3-piperidinyl)methoxy]phenyl}thieno[3,2-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution containing 6-(4-chlorophenyl)-3-(4-hydroxy-3-methoxyphenyl)thieno[3,2-d]pyrimidin-4(3H)-one (77 mg, 0.20 mmol, the preparation of which may be found in Example K1) and 3-(chloromethyl)-1-methylpiperidine (74 mg) was mixed with Cs2CO3 (261 mg, 0.80 mmol) and the resultant mixture was heated at 85° C. for 3 hours. The mixture was then cooled to room temperature, diluted with dichlormethane, washed with a saturated solution of NaHCO3 and brine, dried (MgSO4), and concentrated under reduced pressure. The resultant residue was purified by column chromatography to provide the title compound.

Workup

  1. customthe preparation of which
  2. washwashed with a saturated solution of NaHCO3 and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe resultant residue was purified by column chromatography

Sources & evidence

ORD record
ord-e7f9ea7ad6e842f5a3167c33f34df315
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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