Water → HCID 178506135, compound

HRID 1725596Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([CH:8]2[CH2:10][CH2:9]2)[N:5]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]([F:20])([F:19])[F:18])[N:3]=1.[NH:21]1[C:25]2=[N:26][CH:27]=[CH:28][CH:29]=[C:24]2[C:23]([NH2:30])=[N:22]1.O.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[CH:8]1([C:6]2[N:5]=[C:4]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[C:17]([F:20])([F:19])[F:18])[N:3]=[C:2]([NH:30][C:23]3[C:24]4[C:25](=[N:26][CH:27]=[CH:28][CH:29]=4)[NH:21][N:22]=3)[CH:7]=2)[CH2:10][CH2:9]1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 4-chloro-6-cyclopropyl-2-(2-trifluoromethylphenyl)-pyrimidine (7.00 g, 23.4 mmol, prepared as described above in example 8) and 1H-pyrazolo[3,4-b]pyridin-3-ylamine (9.43 g, 70.3 mmol) in N-methylpyrrolidinone (50 mL) was heated at 130° C. for 12 hours. The residue was cooled, dissolved in N-methylpyrrolidinone (2 mL), poured into water (500 mL) and sodium bicarbonate (15 mL) then filtered, washing with water. Purification by flash chromatography [SiO2, ethyl acetate:hexanes (35:65)] provided the title compound (5.25 g, 57% yield) as a white solid. 1H-NMR (500 MHz, DMSO-d6) δ 13.1 (br s, 1H), 10.5 (br s, 1H), 8.50 (m, 2H), 7.82 (d, J=7.8 Hz, 1H), 7.73 (m, 3H), 7.66 (t, J=7.7 Hz, 1H), 7.12 (m, 1H), 2.07 (m, 1H), 1.02 (m, 2H), 0.97 (m, 2H) ppm; LC-MS 397.22 (M+H); Rt (Method A) 3.412 minutes.

Workup

temperatureThe residue was cooled
filtrationthen filtered
washwashing with water
customPurification by flash chromatography [SiO2, ethyl acetate:hexanes (35:65)]

Sources & evidence

ORD record: ord-4d240a49f862476faa735219928ed99e
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491730B2

Reaction notes

Loading…