3-Hydroxypyridine → HCID 59507577, compound

HRID 1043809Notes

Reaction equation

HRID 1043809 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10](NC3C=NC4C(C=3)=CC=CC=4)[CH:9]=2)=[CH:4][N:3]=1.CC(C)([O-])C.[K+].[N:37]1[CH:42]=[CH:41][CH:40]=[C:39]([OH:43])[CH:38]=1>CS(C)=O>[O:17]1[CH2:18][CH2:19][N:14]([C:12]2[N:13]=[C:8]([C:5]3[CH:4]=[N:3][C:2]([NH2:1])=[N:7][CH:6]=3)[CH:9]=[C:10]([O:43][C:39]3[CH:38]=[N:37][CH:42]=[CH:41][CH:40]=3)[N:11]=2)[CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 23630332HCID 23630332, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 59507577HCID 59507577, compoundYield 42.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

5-(6-chloro-2-morpholinopyrimidin-4-yl)pyrimidin-2-amine (10 mg, 0.034 mmol, prepared as in example 1), potassium tert-butoxide (6 mg, 0.051 mmol), pyridin-3-ol (5 mg, 0.051 mmol) and DMSO (0.5 mL) were all combined together and heated at 110° C. for 2 days. The crude product was purified directly by preparative reverse phase HPLC to give 5-(2-morpholino-6-(pyridin-3-yloxy)pyrimidin-4-yl)pyrimidin-2-amine (5.1 mg, 32%). LC/MS (m/z): 352.1 (MH+), Rt 1.83 minutes.

Workup

  1. customThe crude product was purified directly by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-94bbd370d0d646ac802074cc26858486
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Reaction notes

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