Morpholine → 4-amino-2-morpholin-4-yl-pyrimidine-5-carboxylic Acid

HRID 349676Notes

Reaction equation

HRID 349676 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[C:4](SCC)[N:3]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>>[NH2:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[CH:6][N:5]=[C:4]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[N:3]=1

Participants

3

Reactant 2

HCID 8083MorpholineHCID 2753004-Amino-2-(ethylthio)pyrimidine-5-carboxylic acid

Product 1

HCID 99209194-amino-2-morpholin-4-yl-pyrimidine-5-carboxylic AcidYield 30%

Conditions

Temperature
80 °C

Procedure

A mixture of 4-amino-5-carboxy-2-ethylmercaptopyrimidine (0.35 g, 1.8 mmol) and morpholine (0.5 mL, 10 mmol) was warmed at 80° C. for 4 d and concentrated in vacuo. The residue was purified by flash chromatography (silica gel, 4×7.5 cm, eluted with 97.25/2.5/0.25 acetonitrile/water/acetic acid) to yield the product as a white solid (34 mg, 30%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash chromatography (silica gel, 4×7.5 cm, eluted with 97.25/2.5/0.25 acetonitrile/water/acetic acid)

Sources & evidence

ORD record
ord-2614f90f2dac4518807158d9b486f097
Source dataset
uspto-grants-2007_02
Patent number
US07179912B2

Reaction notes

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