Triethylamine → Methyl-2-chloro-4-[3-(methoxymethyl)-8-azabicyclo[3.2.1]octan-8-yl]-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxylate

HRID 928606Notes

Reaction equation

HRID 928606 reaction equation
[CH3:1][O:2][CH2:3][CH:4]1[CH2:10][CH:9]2[NH:11][CH:6]([CH2:7][CH2:8]2)[CH2:5]1.C(N(CC)CC)C.[Cl:19][C:20]1[N:21]=[C:22](Cl)[C:23]2[C:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[C:27]([C:35]([O:37][CH3:38])=[O:36])[S:26][C:24]=2[N:25]=1>C(O)C.ClCCl.O>[CH3:38][O:37][C:35]([C:27]1[S:26][C:24]2[N:25]=[C:20]([Cl:19])[N:21]=[C:22]([N:11]3[CH:6]4[CH2:7][CH2:8][CH:9]3[CH2:10][CH:4]([CH2:3][O:2][CH3:1])[CH2:5]4)[C:23]=2[C:28]=1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)=[O:36]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 895794673-(Methoxymethyl)-8-azabicyclo[3.2.1]octaneHCID 89579730Methyl 2,4-dichloro-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxylate

Product 1

HCID 89579489Methyl-2-chloro-4-[3-(methoxymethyl)-8-azabicyclo[3.2.1]octan-8-yl]-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxylateYield 104%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

3-(Methoxymethyl)-8-azabicyclo[3.2.1]octane (0.106 g, 0.683 mmol) was dissolved in ethanol (2 mL) and dichloromethane (2 mL). Triethylamine (0.166 mL, 1.18 mmol) and methyl 2,4-dichloro-5-phenyl-thieno[2,3-d]pyrimidine-6-carboxylate (0.200 g, 0.590 mmol) were added and the mixture was stirred at room temperature for 5 hr. It was diluted with dichloromethane (2 mL) and water (2 mL). The layers were separated and the aqueous was extracted with dichloromethane (2×2 mL). The combined organic layers were evaporated to give a yellow oil (281 mg). This was purified by silica chromatography (10 g cartridge; eluent petroleum ether 40-60/ethyl acetate 0 to 20%; all output collected). Fractions corresponding to the main peak were combined and evaporated to give the target compound as a yellow solid (0.177 g). m/z [M+H]+458.0/460.0. Retention time 5.30 min (LCMS method+ve 6 min).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous was extracted with dichloromethane (2×2 mL)
  3. customThe combined organic layers were evaporated

Sources & evidence

ORD record
ord-01fc223edf3c4cfaacfdb88a851fdd13
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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