Hydrochloric Acid → 5-(Pyrimidin-5-yloxy)pyridin-3-amine hydrochloride

HRID 1045815Notes

Reaction equation

HRID 1045815 reaction equation
[N:1]1[CH:6]=[C:5]([O:7][C:8]2[CH:9]=[C:10]([NH:14]C(=O)OC(C)(C)C)[CH:11]=[N:12][CH:13]=2)[CH:4]=[N:3][CH:2]=1.[ClH:22]>O1CCOCC1>[ClH:22].[N:1]1[CH:6]=[C:5]([O:7][C:8]2[CH:9]=[C:10]([NH2:14])[CH:11]=[N:12][CH:13]=2)[CH:4]=[N:3][CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58349145tert-Butyl (5-(pyrimidin-5-yloxy)pyridin-3-yl)carbamate

Product 1

HCID 673111255-(Pyrimidin-5-yloxy)pyridin-3-amine hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 6 (1.1 g, 3.8 mmol, 1.0 eq) was stirred in 4M HCl in Dioxane (19 mL) at rt overnight. The reaction mixture was concentrated in vacuo to give 720 mg (100%) of the title compound as an orange solid: 1H NMR (400 MHz, DMSO-d6) 9.13 (s, 1H), 8.86 (s, 2H), 8.04 (s, 1H), 7.89 (s, 1H), 7.38-7.13 (m, 3H); ES-MS [M+1]+: 189.1

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-fa35b70aa36a4f0d9a4197756e4b7725
Source dataset
uspto-grants-2013_10
Patent number
US08569308B2

Reaction notes

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