Water → 7-[4-(4-Chlorobenzoyl)benzyl]-4-methoxy-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine

HRID 1291215

Reaction equation

HRID 1291215 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:6]2[C:15]([CH3:16])=[CH:14][NH:13][C:7]=2[N:8]=[C:9]([S:11][CH3:12])[N:10]=1.[Cl:17][C:18]1[CH:33]=[CH:32][C:21]([C:22]([C:24]2[CH:31]=[CH:30][C:27]([CH2:28]Br)=[CH:26][CH:25]=2)=[O:23])=[CH:20][CH:19]=1.O>CN(C=O)C>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([C:22]([C:24]2[CH:31]=[CH:30][C:27]([CH2:28][N:13]3[C:7]4[N:8]=[C:9]([S:11][CH3:12])[N:10]=[C:5]([O:4][CH3:3])[C:6]=4[C:15]([CH3:16])=[CH:14]3)=[CH:26][CH:25]=2)=[O:23])=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 98396514-(4-Chlorobenzoyl)benzyl bromideHCID 131876724-methoxy-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 189189827-[4-(4-Chlorobenzoyl)benzyl]-4-methoxy-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidineYield 54.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

In an argon gas stream, 60% sodium hydride-oil (220 mg) was suspended in anhydrous DMF (5 ml) and a powder of 4-methoxy-5-methyl-2-methylthio-7H-pyrrolo[2,3-d]pyrimidine (1.05 g) was added in small portions with ice-cooling and stirring. After completion of addition, the mixture was stirred for 30 minutes and then a solution of 4-(4-chlorobenzoyl)benzyl bromide (1.63 g) in DMF (5 ml) was added. Then, at room temperature, the mixture was stirred for 2 hours. To this reaction mixture was added water (50 ml) and the resulting precipitate was collected by filtration, rinsed with water, dried, and purified by flash column chromatography (silica gel; hexane: ethyl acetate=9:1) to provide the title compound (1.19 g). 1H-NMR (CDCl3) δ: 2.33(3H,d,J=1.2Hz), 2.60(3H,s), 4.08(3H,s), 5.36(2H,s), 6.57(1H,d,J=1.2Hz), 7.28(2H,d,J=8.6Hz), 7.44(2H,d,J=8.6Hz), 7.70(2H,d,J=8.6Hz), 7.72(2H,d,J=8.6Hz).

Workup

  1. temperaturecooling
  2. additionAfter completion of addition
  3. stirringthe mixture was stirred for 30 minutes
  4. stirringThen, at room temperature, the mixture was stirred for 2 hours
  5. filtrationthe resulting precipitate was collected by filtration
  6. washrinsed with water
  7. customdried
  8. custompurified by flash column chromatography (silica gel; hexane: ethyl acetate=9:1)

Sources & evidence

ORD record
ord-dffd02a655a046fcba243f47026212fe
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Linked notes

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