Hydrochloric Acid → 4-(2-Methylsulfanylpyrimidin-4-yloxy)-naphthalen-1-ylamine

HRID 1641286Notes

Reaction equation

HRID 1641286 reaction equation
C(OC(=O)[NH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([S:25][CH3:26])[N:20]=2)=[CH:10][CH:9]=1)(C)(C)C.Cl>O1CCOCC1>[CH3:26][S:25][C:21]1[N:20]=[C:19]([O:18][C:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:8]([NH2:7])=[CH:9][CH:10]=2)[CH:24]=[CH:23][N:22]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59553280t-Butyl(4-{[2-(methylthio)pyrimidin-4-yl]oxy}-1-naphthyl)carbamate

Product 1

HCID 595533854-(2-Methylsulfanylpyrimidin-4-yloxy)-naphthalen-1-ylamineYield 151.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred solution of [4-(2-methylsulfanylpyrimidin-4-yloxy)-naphthalen-1-yl]-carbamic acid tert-butyl ester (1.375 g, 3.6 mmol) in anhydrous dioxane (10 ml) at room temperature is added 4M HCl in dioxane (12 ml, 48 mmol). After 1 day the mixture is evaporated to dryness to give 4-(2-methylsulfanylpyrimidin-4-yloxy)-naphthalen-1-ylamine as a light purple powder (1.547 g).

Workup

  1. customAfter 1 day the mixture is evaporated to dryness

Sources & evidence

ORD record
ord-ea41be0eb86447c09b468ef8933d74cb
Source dataset
uspto-grants-2012_02
Patent number
US08114873B2

Reaction notes

Loading…