Diisopropylethylamine → HCID 67112048, compound

HRID 2088890Notes

Reaction equation

HRID 2088890 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][C:9](=[O:17])[N:10]([CH2:12][C:13]([F:16])([F:15])[F:14])[CH2:11][C:3]=12.Cl.Cl.[CH2:20]([C:22]1[N:23]=[C:24]([CH:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[N:25]([CH2:27][CH2:28][OH:29])[CH:26]=1)[CH3:21].C(N(C(C)C)CC)(C)C>CO>[CH2:20]([C:22]1[N:23]=[C:24]([CH:30]2[CH2:31][CH2:32][N:33]([C:2]3[N:7]=[CH:6][N:5]=[C:4]4[NH:8][C:9](=[O:17])[N:10]([CH2:12][C:13]([F:16])([F:15])[F:14])[CH2:11][C:3]=34)[CH2:34][CH2:35]2)[N:25]([CH2:27][CH2:28][OH:29])[CH:26]=1)[CH3:21]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 67112246HCID 67112246, compoundHCID 86666562HCID 86666562, compound

Product 1

HCID 67112048HCID 67112048, compoundYield 140.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
150 °C

Procedure

Add 5-chloro-3-(2,2,2-trifluoroethyl)-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (0.28 g, 1.05 mmol), 2-(4-ethyl-2-(piperidin-4-yl)-1H-imidazol-1-yl)ethanol dihydrochloride (0.38 g, 1.3 eq), methanol (15 mL) and diisopropylethylamine (0.91 mL, 5.0 eq) into a 20 mL microwave vial. Seal the tube and heat in a microwave reactor to 150° C., for 1 hour. Filter through silica gel, eluting with 10% ammonia-methanol/dichloromethane. Concentrate the filtrate in vacuo. Purify by silica gel chromatography, eluting with 3:1 ethyl acetate/methanol, to give the title compound as a yellow foam (0.67 g, 70%). MS (ES) m/z=454 [M]+.

Workup

  1. customSeal the tube
  2. filtrationFilter through silica gel
  3. washeluting with 10% ammonia-methanol/dichloromethane
  4. concentrationConcentrate the filtrate in vacuo
  5. customPurify by silica gel chromatography
  6. washeluting with 3:1 ethyl acetate/methanol

Sources & evidence

ORD record
ord-2b73a62f4b814a35804ad8220cdf793f
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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