4-(4,6-Dichloropyrimidin-2-yl)morpholine → 4-(6-Chloropyrimidin-4-yl)morpholine

HRID 594055

Reaction equation

HRID 594055 reaction equation
[Cl:1][C:2]1C=C(Cl)[N:5]=[C:4](N2CCOCC2)[N:3]=1.[NH:15]1[CH2:20][CH2:19]S(=O)(=O)[CH2:17][CH2:16]1.[CH3:23][CH2:24][OH:25].C1COCC1>>[Cl:1][C:2]1[N:3]=[CH:4][N:5]=[C:16]([N:15]2[CH2:23][CH2:24][O:25][CH2:19][CH2:20]2)[CH:17]=1

Participants

4

Reactant 3

HCID 27720684-(4,6-Dichloropyrimidin-2-yl)morpholineHCID 6484228Thiomorpholine 1,1-dioxideHCID 21873804Tetrahydrofuran ethanol

Product 1

HCID 7960704-(6-Chloropyrimidin-4-yl)morpholineYield 97%

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(4,6-dichloropyrimidin-2-yl)morpholine (1.0 equiv.) in EtOH:THF (1:1, 0.25 M) was added thiomorpholine 1,1-dioxide (1.0 equiv.) in one portion. The resulting mixture was heated to 100° C. for 42 h. The resulting mixture was then cooled to RT and concentrated in vacuo to yield an off white solid in The reaction mixture was then concentrated in vacuo and dried under high vacuum over 20 h to yield 4-(6-chloropyrimidin-4-yl)morpholine as a white solid in 97% yield. LCMS (m/z) (M+H)=333.0/334.9, Rt=0.68 min.

Workup

  1. temperatureThe resulting mixture was then cooled to RT
  2. concentrationconcentrated in vacuo
  3. customto yield an off white solid in The reaction mixture
  4. concentrationwas then concentrated in vacuo
  5. customdried under high vacuum over 20 h

Sources & evidence

ORD record
ord-8165ba03c8f2474a8cbd2fc4e09fe009
Source dataset
uspto-grants-2016_01
Patent number
US09242969B2

Linked notes

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