Triethylamine → 4-(6-Chloro-2-morpholinopyrimidin-4-yl)-2,2-dimethylmorpholine

HRID 594062

Reaction equation

HRID 594062 reaction equation
[CH3:1][C:2]1([CH3:8])[O:7][CH2:6][CH2:5][NH:4][CH2:3]1.[Cl:9][C:10]1[CH:15]=[C:14](Cl)[N:13]=[C:12]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:11]=1.C(N(CC)CC)C>CCO>[Cl:9][C:10]1[N:11]=[C:12]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:13]=[C:14]([N:4]2[CH2:5][CH2:6][O:7][C:2]([CH3:8])([CH3:1])[CH2:3]2)[CH:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27720684-(4,6-Dichloropyrimidin-2-yl)morpholineHCID 189596742,2-Dimethylmorpholine

Product 1

HCID 904095494-(6-Chloro-2-morpholinopyrimidin-4-yl)-2,2-dimethylmorpholine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2,2-dimethylmorpholine (2.0 equiv.), 4-(4,6-dichloropyrimidin-2-yl)morpholine (1 equiv.) and triethylamine (6 equiv.) in EtOH (0.2 M) were heated to 110° C. for 25 min in the microwave. The reaction mixture was partitioned between EtOAc and water. The organic phase was dried over sodium sulfate. The resulting solution was concentrated and dried under vacuo to give 4-(6-chloro-2-morpholinopyrimidin-4-yl)-2,2-dimethylmorpholine and was used in the next step without further purification. LCMS (m/z) (M+H)=313.2, Rt=0.86 min.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationThe resulting solution was concentrated
  4. customdried under vacuo

Sources & evidence

ORD record
ord-4511474057dd4666a0129689127ff48e
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Linked notes

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