Morpholine → 1-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-3,3-dimethyl-butan-2-ol

HRID 528478Notes

Reaction equation

HRID 528478 reaction equation
[CH3:1][C:2]([CH3:17])([CH3:16])[CH:3]([OH:15])[CH2:4][O:5][C:6]1[C:7](Cl)=[N:8][C:9]([Cl:13])=[N:10][C:11]=1[Cl:12].C(N(CC)CC)C.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>>[Cl:13][C:9]1[N:10]=[C:11]([Cl:12])[C:6]([O:5][CH2:4][CH:3]([OH:15])[C:2]([CH3:1])([CH3:17])[CH3:16])=[C:7]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[N:8]=1

Participants

4

Reactant 3

HCID 8083MorpholineHCID 8471TriethylamineHCID 867117593,3-Dimethyl-1-(2,4,6-trichloro-pyrimidin-5-yloxy)-butan-2-ol

Product 1

HCID 867117601-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-3,3-dimethyl-butan-2-olYield 77%

Procedure

To a solution of 3,3-dimethyl-1-(2,4,6-trichloro-pyrimidin-5-yloxy)-butan-2-ol (275 mg, 1.05 mmol) in IMS (3 mL) was added triethylamine (291 μL, 2.09 mmol) followed by morpholine (100 μL, 1.15 mmol) and stirred at RT for 2 hours. The reaction was quenched with saturated aqueous sodium hydrogen carbonate solution then extracted with ethyl acetate. The combined organic extracts were dried (Na2SO4) then concentrated in vacuo giving 1-(2,4-Dichloro-6-morpholin-4-yl-pyrimidin-5-yloxy)-3,3-dimethyl-butan-2-ol (255 mg, 77%). LCMS: RT=3.57 min, [M+H]+=350/352/354.

Workup

  1. customThe reaction was quenched with saturated aqueous sodium hydrogen carbonate solution
  2. extractionthen extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-d7ca4868660d4027af6b5eb6ca9b7431
Source dataset
uspto-grants-2016_05
Patent number
US09346817B2

Reaction notes

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