1,4-Dioxane → HCID 69066824, compound

HRID 1785446Notes

Reaction equation

HRID 1785446 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.[NH2:28][CH:29]([CH3:39])[CH2:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][OH:38])=[CH:33][CH:32]=1.O1CCOCC1>CN1CCCC1=O>[OH:38][CH2:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][CH:29]([NH:28][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)[CH3:39])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 13938670HCID 13938670, compoundHCID 69066107HCID 69066107, compound

Product 1

HCID 69066824HCID 69066824, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

1-(2-methanesulfonyl-pyrimidin-4-yl)-8-phenyl-1,2,3,6-tetrahydro-pyrimido[1,2-a]pyrimidin-4-one (1.1 g, 2.9 mmol) and [4-(2-amino-propyl)-phenyl]-methanol (0.96 g, 5.8 mmol) in 1:1 dioxane: 1-methyl-2-pyrrolidinone (16 mL) was heated to 100° C. for 20 h. The mixture was partitioned between water (30 mL) and ethyl acetate (60 mL). The organic phase was separated, washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate and chromatographed on silica gel using 0-8% 2M NH3 MeOH/CH2Cl2 to afford a white solid. M+1=469. 1NMR (CDCl3) d (3H, 1.21 ppm), s (1H, 1.79 ppm), m (2H, 2.22 ppm), m(1H, 2.79 ppm), m (1H, 2.98 ppm), m (4H, 4.11 ppm), m (1H, 4.13 ppm), b(3H, 4.68 ppm), s (1H, 6.60 ppm), d (2H, 7.21 ppm), d (3H, 7.29 ppm), m (3H, 7.44 ppm), dd (2H, 7.91 ppm), d (1H, 8.17 ppm).

Workup

  1. customThe mixture was partitioned between water (30 mL) and ethyl acetate (60 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 0-8% 2M NH3 MeOH/CH2Cl2
  6. customto afford a white solid

Sources & evidence

ORD record
ord-ef3eca606b604be5a9ee6c58e663f477
Source dataset
uspto-grants-2009_03
Patent number
US07504403B2

Reaction notes

Loading…