Water → HCID 118436035, compound

HRID 1775496Notes

Reaction equation

HRID 1775496 reaction equation
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][NH:3]1.Cl[C:9]1[N:14]=[C:13]([O:15][CH3:16])[CH:12]=[C:11]([O:17][CH3:18])[N:10]=1.CCN(C(C)C)C(C)C.O>CS(C)=O>[CH3:18][O:17][C:11]1[CH:12]=[C:13]([O:15][CH3:16])[N:14]=[C:9]([N:3]2[CH2:4][CH2:5][O:6][CH2:7][C@@H:2]2[CH3:1])[N:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 51523232-Chloro-4,6-dimethoxypyrimidineHCID 12012220(3S)-3-methylmorpholine

Product 1

HCID 118436035HCID 118436035, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of (S)-3-methylmorpholine (4.86 g, 48.0 mmol), 2-chloro-4,6-dimethoxypyrimidine (6.98 g, 40 mmol) and DIPEA (8.36 mL, 48.0 mmol) in DMSO (40 mL) was heated at 100° C. in a sealed flask for 22 h, and then allowed to cool to room temperature. The reaction mixture was placed in an ice bath, and water (120 mL) was added drop-wise. The mixture was decanted and the gummy precipitate was dissolved in ethyl acetate. The ethyl acetate solution was washed with brine, dried with MgSO4, filtered and concentrated by rotary evaporation to give the title compound (8.58 g, 90%). 1H NMR (400 MHz, CDCl3) δ 5.40 (s, 1 H), 4.69 (qd, J=6.8, 3.1 Hz, 1 H), 4.33 (dd, J=13.7, 2.9 Hz, 1 H), 4.01-3.93 (m, 1 H), 3.86 (s, 6 H), 3.78-3.73 (m, 1 H), 3.73-3.66 (m, 1 H), 3.54 (ddd, J=12.2, 11.4, 3.1 Hz, 1 H), 3.25 (ddd, J=13.5, 12.4, 3.8 Hz, 1 H), 1.29 (d, J=6.8 Hz, 3 H). m/z (APCI+) for C11H17N3O3 240.0 (M+H)+.

Workup

  1. customThe reaction mixture was placed in an ice bath
  2. customThe mixture was decanted
  3. dissolutionthe gummy precipitate was dissolved in ethyl acetate
  4. washThe ethyl acetate solution was washed with brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-d826e3abd00f424a9cf8ae1046f180f2
Source dataset
uspto-grants-2016_02
Patent number
US09260439B2

Reaction notes

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