1,4-Dioxane → HCID 69064384, compound

HRID 1785445Notes

Reaction equation

HRID 1785445 reaction equation
CS([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][C:14](=[O:17])[N:13]3[CH2:18][CH:19]=[C:20]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[N:21]=[C:12]23)[CH:8]=[CH:7][N:6]=1)(=O)=O.[C:28]([O:32][C:33](=[O:46])[NH:34][CH:35]([C:37]1[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][NH2:45])=[CH:39][CH:38]=1)[CH3:36])([CH3:31])([CH3:30])[CH3:29].O1CCOCC1>CN1CCCC1=O>[C:28]([O:32][C:33](=[O:46])[NH:34][CH:35]([C:37]1[CH:42]=[CH:41][C:40]([CH2:43][CH2:44][NH:45][C:5]2[N:10]=[C:9]([N:11]3[CH2:16][CH2:15][C:14](=[O:17])[N:13]4[CH2:18][CH:19]=[C:20]([C:22]5[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=5)[N:21]=[C:12]34)[CH:8]=[CH:7][N:6]=2)=[CH:39][CH:38]=1)[CH3:36])([CH3:30])([CH3:29])[CH3:31]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 69063910HCID 69063910, compoundHCID 69066107HCID 69066107, compound

Product 1

HCID 69064384HCID 69064384, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The mixture of 1-(2-methanesulfonyl-pyrimidin-4-yl)-8-phenyl-1,2,3,6-tetrahydro -pyrimido[1,2-a]pyrimidin-4-one (0.20 g, 053 mmol) and {1-[4-(2-amino -ethyl)-phenyl]-ethyl}-carbamic acid tert-butyl ester (0.304 g, 0.79 mmol) in 1:1 dioxane: 1-methyl -2-pyrrolidinone (6 mL) was heated to 100° C. for 17 h. The mixture was partitioned between water (10 mL) and ethyl acetate (20 mL). The organic phase was separated, washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate and chromatographed on silica gel using 0-4% MeOH/CH2Cl2to afford a white solid. M+1=568.

Workup

  1. customThe mixture was partitioned between water (10 mL) and ethyl acetate (20 mL)
  2. customThe organic phase was separated
  3. washwashed with water, saturated sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. customchromatographed on silica gel using 0-4% MeOH/CH2Cl2to
  6. customafford a white solid

Sources & evidence

ORD record
ord-da297c3cf29b4412bf3fcc93f12a5406
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

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