Isopropanol → HCID 11554622, compound

HRID 1517391Notes

Reaction equation

HRID 1517391 reaction equation
Cl[C:2]1[C:3]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[O:22]([CH2:29][CH2:30]N1CCNCC1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH:37](O)([CH3:39])C>>[O:22]([CH2:29][CH2:30][CH:39]1[CH2:37][NH:11][CH2:3][CH2:4][N:5]1[C:2]1[C:3]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)[CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 2331871-(2-Phenoxyethyl)piperazineHCID 714077034-Chloro-6-(3,4-dimethoxyphenyl)pyrido[3,2-d]pyrimidine

Product 1

HCID 11554622HCID 11554622, compoundYield 84%

Conditions

Temperature
80 °C

Procedure

To a suspension of 4-chloro-6-(3,4-dimethoxyphenyl)-pyrido[3,2-d]pyrimidine (120 mg, 0.398 mmol) in isopropanol (15 ml) was added 1-(2-phenoxyethyl)-piperazine (0.795 mmol, 164 mg). The suspension was stirred at 80° C., after which the suspension became a clear colourless solution. The solvents were evaporated in vacuo. The residue was redissolved in ethyl acetate and extracted with a NaOH solution (1 N). The combined organic layers were evaporated in vacuo and purified by silica gel column chromatography (the mobile phase being a mixture of methanol and dichloromethane in a ratio gradually ranging from 1:99 to 2:98), resulting in the title compound (157 mg, yield 84%) which was characterised by its mass spectrum as follows: MS (m/z): 472 ([M+H]+, 100).

Workup

  1. customThe solvents were evaporated in vacuo
  2. dissolutionThe residue was redissolved in ethyl acetate
  3. extractionextracted with a NaOH solution (1 N)
  4. customThe combined organic layers were evaporated in vacuo
  5. custompurified by silica gel column chromatography (the mobile phase
  6. additiona mixture of methanol and dichloromethane in a ratio

Sources & evidence

ORD record
ord-76ac69c47a8447d691b41098f7c7bb43
Source dataset
uspto-grants-2012_07
Patent number
US08232278B2

Reaction notes

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