Potassium Carbonate → HCID 57530538, compound

HRID 1454477Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])[N:5]=[C:4]2[N:14]([C:19]3[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=3[F:26])[C:15](=[O:18])[NH:16][CH2:17][C:3]=12.[CH3:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([OH:34])=[O:33])=[CH:30][C:29]=1B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[F:26][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([F:25])[C:19]=1[N:14]1[C:4]2[N:5]=[C:6]([NH:8][CH2:9][CH2:10][N:11]([CH3:13])[CH3:12])[N:7]=[C:2]([C:29]3[CH:30]=[C:31]([CH:35]=[CH:36][C:28]=3[CH3:27])[C:32]([OH:34])=[O:33])[C:3]=2[CH2:17][NH:16][C:15]1=[O:18]

Participants

Conditions

Temperature: 150 °C

Procedure

To the solution of 5-chloro-1-(2,6-difluorophenyl)-7-{[2-(dimethylamino)ethyl]amino}-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one (191 mg, 0.50 mmol) in dioxane (15 mL) and water (5 mL) were added 4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (197 mg, 0.75 mmol), K2CO3 (415 mg, 3.0 mmol) and tetrakis(triphenyl-phosphine)palladium(0) (23 mg, 0.025 mmol). The reaction mixture was heated to 150° C. for about 15 minutes with microwave. The reaction mixture was concentrated to dry then was added DMSO (2 mL), water (0.5 mL) and HOAc (1 drop). The solution was filtered and applied to the reverse phase HPLC to afford the titled compound 0.24 g (quantitative). LC-MS m/z 483 (M+H)+; 1H-NMR (CD3OD) 2.36 (s, 3 H), 2.76 (s, 6H), 3.16 (s, 2 H), 3.56 (s, 2 H), 4.13 (s, 2 H), 7.21 (m, 1 H), 7.53 (m, 2 H), 7.95 (s, 1 H), 8.09 (d, J=7.6 Hz, 1 H).

Workup

concentrationThe reaction mixture was concentrated
customto dry
additionthen was added DMSO (2 mL), water (0.5 mL) and HOAc (1 drop)
filtrationThe solution was filtered

Sources & evidence

ORD record: ord-f7c13d7006ab4e8db9bf0a7156fb0244
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07479558B2

Reaction notes

Loading…