3,4,5-Trimethoxyaniline → N4-(5-tert-butylisoxazol-3-yl)-N2-(3,4,5-trimethoxy-phenyl)-pyrimidine-2,4-diamine

HRID 1241589Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[O:11][N:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:18][O:19][C:20]1[CH:21]=[C:22]([CH:24]=[C:25]([O:29][CH3:30])[C:26]=1[O:27][CH3:28])[NH2:23].N(CC)(CC)CC.FC(C(O)=O)(F)F>CS(C)=O>[C:14]([C:12]1[O:11][N:10]=[C:9]([NH:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:23][C:22]3[CH:24]=[C:25]([O:29][CH3:30])[C:26]([O:27][CH3:28])=[C:20]([O:19][CH3:18])[CH:21]=3)[N:7]=2)[CH:13]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (2-chloropyrimidin-4-yl)-(5-tert-butyl-isoxazol-3-yl)amine (50 mg 0.198 mmol Step A) and 3,4,5-trimethoxyaniline (36.2 mg 0.198 mmol) was suspended in 0.15 mL of a 2M solution of Et3N-TFA in DMSO (stock solution prepared by combining 1.28 g of Et3N-TFA and 3 mL of DMSO) in a sealed tube. The resulting mixture was heated at 100° C. for 4 h, cooled to RT, diluted with CH2C12 (attempted crystallization), concentrated and purified via preparative HPLC to give N4-(5-tert-butylisoxazol-3-yl)-N2-(3,4,5-trimethoxy-phenyl)-pyrimidine-2,4-diamine as a green-gray amorphous solid. MS m/z=400. Calc'd for C20H25N5O4— 399.19.

Workup

temperaturecooled to RT
additiondiluted with CH2C12 (attempted crystallization)
concentrationconcentrated
custompurified via preparative HPLC

Sources & evidence

ORD record: ord-c30c3eae67e44923acbdd3f2901c2fb8
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115617B2

Reaction notes

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