Dimethyl Sulfoxide → N2-(3-Ethynylphenyl)-N4-(3-quinolinyl)-2,4-pyrimidinediamine

HRID 495453Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (2-chloro-pyrimidin-4-yl)-quinolin-3-yl-amine (70 mg 0.272 mmol) and 3-ethynylaniline (33 mg, 0.282 mmol) was suspended in a sealed tube with 0.3 mL of DMSO. The resulting mixture was heated at 100° C. for 2 h, cooled to RT, diluted with CH2Cl2. The precipitate was collected by suction filtration then dried under vacuum to give the desired product as an off-white solid. M+H—338; Calc'd for C21H15N5: 337.13.

Workup

temperaturecooled to RT
filtrationThe precipitate was collected by suction filtration
customthen dried under vacuum

Sources & evidence

ORD record: ord-f0d37dfdfb1c4a55877dfa267a219b3a
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06939874B2

Reaction notes

Loading…