Water → 2-Amino-4,6-bis-(pyridin-2-ylmethoxy)-pyrimidine-5-carbonitrile

HRID 1356153Notes

Reaction equation

HRID 1356153 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]#[N:10])=[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[N:3]=1.[OH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1.C1CCN2C(=NCCC2)CC1.O>COCCOC>[NH2:1][C:2]1[N:7]=[C:6]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:5]([C:9]#[N:10])=[C:4]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11474PiconolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 185074852-Amino-4-chloro-6-(pyridin-2-ylmethoxy)-pyrimidine-5-carbonitrile

Product 1

HCID 185075132-Amino-4,6-bis-(pyridin-2-ylmethoxy)-pyrimidine-5-carbonitrileYield 48%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred suspension of 130 mg (0.50 mmol) 2-amino-4-chloro-6-(pyridin-2-ylmethoxy)-pyrimidine-5-carbonitrile in 10 ml DME were added 0.17 ml (1.74 mmol) 2-(hydroxymethyl)pyridine and 0.11 ml (0.75 mmol) DBU and stirring continued for 1 hour at room temperature. 50 ml water was then added and the resulting crystals collected by filtration and washed with ether to afford 80 mg (48%) 2-amino-4,6-bis-(pyridin-2-ylmethoxy)-pyrimidine-5-carbonitrile as a white crystalline solid. ES-MS m/e (%): 357 (M+Na+, 40), 335 (M+H+, 100).

Workup

  1. filtrationthe resulting crystals collected by filtration
  2. washwashed with ether

Sources & evidence

ORD record
ord-714617e0b6614638aa11037ed8f0d1e8
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

Loading…