Morpholine → (4-Methoxy-6-morpholin-4-ylpyrimidin-2-yl)acetic acid ethyl ester

HRID 2278582Notes

Reaction equation

HRID 2278582 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[N:11]=[C:10](Cl)[CH:9]=[C:8]([O:13][CH3:14])[N:7]=1)[CH3:2].[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>>[CH2:1]([O:3][C:4](=[O:15])[CH2:5][C:6]1[N:7]=[C:8]([O:13][CH3:14])[CH:9]=[C:10]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[N:11]=1)[CH3:2]

Participants

3

Reactant 2

HCID 8083MorpholineHCID 86699270Ethyl 2-(4-chloro-6-methoxypyrimidin-2-yl)acetate

Product 1

HCID 86699276(4-Methoxy-6-morpholin-4-ylpyrimidin-2-yl)acetic acid ethyl ester

Procedure

1.5 g of (4-chloro-6-methoxypyrimidin-2-yl)acetic acid ethyl ester and 20 ml of morpholine are mixed together in a microwave tube. After microwave irradiation for 1 h at 90° C., the reaction mixture is concentrated under reduced pressure and then diluted with 300 ml of ethyl acetate and 300 ml of water. After settling out, the organic phase is dried over magnesium sulfate, filtered, and then concentrated under reduced pressure. 1.9 g of (4-methoxy-6-morpholin-4-ylpyrimidin-2-yl)acetic acid ethyl ester are thus obtained in the form of a viscous oil which crystallizes and which is used as it is in the next step.

Workup

  1. customAfter microwave irradiation for 1 h at 90° C.
  2. concentrationthe reaction mixture is concentrated under reduced pressure
  3. additiondiluted with 300 ml of ethyl acetate and 300 ml of water
  4. dry with materialthe organic phase is dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6d774c6aa84c41fe889eaa301b69859f
Source dataset
uspto-grants-2015_09
Patent number
US09133168B2

Reaction notes

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