Phenol → 6-(4-chlorophenyl)-3-{3-[(1-methylpiperidin-4-yl)oxy]benzyl}thieno[3,2-d]pyrimidin-4(3H)-one

HRID 2239323Notes

Reaction equation

HRID 2239323 reaction equation
CO[C:3]([C:5]1[S:6][C:7]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)=[CH:8][C:9]=1[N:10]=[CH:11][N:12]([CH3:14])C)=[O:4].[CH3:22][N:23]1[CH2:28][CH2:27][CH:26]([O:29][C:30]2[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=2)CN)[CH2:25][CH2:24]1.C1(O)C=CC=CC=1>>[Cl:21][C:18]1[CH:17]=[CH:16][C:15]([C:7]2[S:6][C:5]3[C:3](=[O:4])[N:12]([CH2:14][C:36]4[CH:35]=[CH:32][CH:31]=[C:30]([O:29][CH:26]5[CH2:25][CH2:24][N:23]([CH3:22])[CH2:28][CH2:27]5)[CH:37]=4)[CH:11]=[N:10][C:9]=3[CH:8]=2)=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 996PhenolHCID 11544322Methyl 5-(4-chlorophenyl)-3-(dimethylaminomethyleneamino)thiophene-2-carboxylateHCID 392028503-(1-Methyl-piperidin-4-yloxy)-benzylamine

Product 1

HCID 247852716-(4-chlorophenyl)-3-{3-[(1-methylpiperidin-4-yl)oxy]benzyl}thieno[3,2-d]pyrimidin-4(3H)-one

Procedure

5-(4-Chloro-phenyl)-3-(dimethylamino-methyleneamino)-thiophene-2-carboxylic acid methyl ester (0.100 g, 0.310 mmol), 3-(1-methyl-piperidin-4-yloxy)-benzylamine (0.109 g, 0.370 mmol) and phenol (1.0 g) were stirred at 130° C. for 2 hours. The reaction mixture was allowed to cool to r.t. and the product was partially purified by flash chromatography using a gradient elution with n-heptane against MeOH/TEA. The fractions containing the title product were concentrated in vacuo and purified further by washing with MeOH to give the title compound. Yield: 0.052 g (36%). 1H NMR (400 MHz, CDCl3) δ 8.08 (s, 1H), 7.61 (d, 2H, J=8.52 Hz), 7.45 (s, 1H), 7.41 (d, 2H, J=8.52 Hz), 7.24 (m, 1H), 6.89 (m, 2H), 6.83 (d, 1H, J=9.02 Hz), 5.16 (s, 2H), 4.29 (bs, 1H), 2.65 (bs, 2H), 2.21-2.31 (m, 5H), 1.95 (m, 2H), 1.79 (m, 2H). MS (ESI+) 465.93 (M+1H+).

Workup

  1. customthe product was partially purified by flash chromatography
  2. washa gradient elution with n-heptane against MeOH/TEA
  3. additionThe fractions containing the title product
  4. concentrationwere concentrated in vacuo
  5. custompurified further
  6. washby washing with MeOH

Sources & evidence

ORD record
ord-83d1961e898c47d6bd366e8eedc7793f
Source dataset
uspto-grants-2010_05
Patent number
US07723331B2

Reaction notes

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