5-(5-Amino-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine → 5-(2-Isopropyl-4-methoxy-5-[1,2,3]triazol-1-yl-phenoxy)-pyrimidine-2,4-diamine

HRID 81786Notes

Reaction equation

[NH2:1][C:2]1[C:3]([O:20][CH3:21])=[CH:4][C:5]([CH:17]([CH3:19])[CH3:18])=[C:6]([CH:16]=1)[O:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1.S(C1C=CC(C)=CC=1)(O)(=O)=O.Cl[C:34]([NH:37][NH2:38])(Cl)[CH3:35].NN>CO>[CH:17]([C:5]1[CH:4]=[C:3]([O:20][CH3:21])[C:2]([N:1]2[CH:35]=[CH:34][N:37]=[N:38]2)=[CH:16][C:6]=1[O:7][C:8]1[C:9]([NH2:15])=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1)([CH3:19])[CH3:18]

Participants

Conditions

Temperature: 50 °C

Procedure

Following the procedure of Harada et al., Heterocycles 1998, 48, 695-702, to a solution of 5-(5-amino-2-isopropyl-4-methoxy-phenoxy)-pyrimidine-2,4-diamine (0.400 g, 1.8 mmol) in 5 ml methanol at 0° C. was added trimethylamime (0.308 g, 3.0 mmol) and hydrazine 1,1-dichloroethyl hydrazine tosylate (0.388 g, 1.4 mmol). The solution was warmed to 50° C. After 4 h the mixture was concentrated in vacuo and extracted with CH2Cl2. The combined organics were washed with H2O, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. Purification via flash chromatography (94:6 CH2Cl2/MeOH) afforded 5-(2-isopropyl-4-methoxy-5-[1,2,3]triazol-1-yl-phenoxy)-pyrimidine-2,4-diamine (0.145 g, 31%) as a white solid; [MH]+=342.

Workup

concentrationAfter 4 h the mixture was concentrated in vacuo
extractionextracted with CH2Cl2
washThe combined organics were washed with H2O
washwashed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customPurification via flash chromatography (94:6 CH2Cl2/MeOH)

Sources & evidence

ORD record: ord-3f4dcbed7ea346d3b3d901a8a6ad0084
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846705B2

Reaction notes

Loading…