Water → 2-Amino-4-chloro-6-(3-methyl-pyridin-2-ylmethoxy)-pyrimidine-5-carbonitrile

HRID 1356140Notes

Reaction equation

HRID 1356140 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[C:4](S(C)=O)[N:3]=1.[CH3:14][C:15]1[C:16]([CH2:21][OH:22])=[N:17][CH:18]=[CH:19][CH:20]=1.C1CCN2C(=NCCC2)CC1.O>COCCOC>[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]#[N:10])=[C:4]([O:22][CH2:21][C:16]2[C:15]([CH3:14])=[CH:20][CH:19]=[CH:18][N:17]=2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1514369(3-Methylpyridin-2-yl)methanolHCID 185072772-Amino-4-chloro-6-methanesulfinyl-pyrimidine-5-carbonitrile

Product 1

HCID 185072242-Amino-4-chloro-6-(3-methyl-pyridin-2-ylmethoxy)-pyrimidine-5-carbonitrileYield 35%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a stirred suspension of 50 mg (0.23 mmol) 2-amino-4-chloro-6-methanesulfinyl-pyrimidine-5-carbonitrile in 1 ml DME were added 28 mg (0.23 mmol) 3-methyl-2-pyridinemethanol and 521l (0.35 mmol) DBU and stirring continued for 30 min at room temperature. 5 ml water was then added and the resulting crystals collected by filtration and washed with ether to afford 22 mg (35%) 2-amino-4-chloro-6-(3-methyl-pyridin-2-ylmethoxy)-pyrimidine-5-carbonitrile as a white crystalline solid. ES-MS m/e (%): 278 (M{37Cl}+H+, 35), 276 (M{35Cl}+H+, 100).

Workup

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

Sources & evidence

ORD record
ord-6115d30aee184e96a9ca34ca0df71324
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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