Acetonitrile → 7-(4-(2-morpholinoethylamino)-3-(methylsulfonyl)phenyl)-5-(isopropylamino)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1023302Notes

Reaction equation

HRID 1023302 reaction equation
Cl[C:2]1[N:11]=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[C:9]2[C:8](=[O:16])[N:7]([CH3:17])[CH:6]=[N:5][C:4]=2[CH:3]=1.CC1(C)C(C)(C)OB([C:26]2[CH:31]=[CH:30][C:29]([NH:32][CH2:33][CH2:34][N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)=[C:28]([S:41]([CH3:44])(=[O:43])=[O:42])[CH:27]=2)O1.C([O-])([O-])=O.[Na+].[Na+].C(#N)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[O:38]1[CH2:37][CH2:36][N:35]([CH2:34][CH2:33][NH:32][C:29]2[CH:30]=[CH:31][C:26]([C:2]3[N:11]=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[C:9]4[C:8](=[O:16])[N:7]([CH3:17])[CH:6]=[N:5][C:4]=4[CH:3]=3)=[CH:27][C:28]=2[S:41]([CH3:44])(=[O:42])=[O:43])[CH2:40][CH2:39]1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 10340Sodium CarbonateHCID 580929447-Chloro-5-(isopropylamino)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-oneHCID 669600504-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(methylsulfonyl)-N-(2-morpholinoethyl)benzenamine

Product 1

HCID 669587777-(4-(2-morpholinoethylamino)-3-(methylsulfonyl)phenyl)-5-(isopropylamino)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

7-Chloro-5-(isopropylamino)-3-methylpyrido[4,3-d]pyrimidin-4(3H)-one (60 mg, 0.24 mmol), crude 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-(methylsulfonyl)-N-(2-morpholinoethyl)benzenamine (240 mg, ˜0.28 mmol), Pd(PPh3)4 (28 mg, 0.024 mmol) and Na2CO3 (102 mg, 0.96 mol) in a mixed solvent of acetonitrile (4 mL) and H2O (4 mL) were added to a 20 mL microwave tube and sealed. The tube was then heated in a Microwave Reactor at 140° C. for 10 minutes. The solvent was removed and the crude product purified by silica column using 7% MeOH in DCM to give the final product as a pale solid. ESI-MS m/z 501.2 (MH+); 1H NMR (DMSO-d6) δ 8.71 (d, J=7.2 Hz, 1H), 8.46 (d, J=2.4 HZ, 1H), 8.40 (s, 1H), 8.26 (d, J=8.8 Hz, 1H), 7.04 (s, 1H), 6.97 (d, J=8.8 Hz, 1H), 6.77 (t, J=4.8 Hz, 1H), 3.59 (m, 4H), 3.42 (s, 3H), 3.33 (m, 4H), 3.20 (s, 3H), 2.62 (m, 2H), 2.44 (s, 3H), 1.29 (d, J=6.4 Hz, 6H).

Workup

  1. customsealed
  2. customThe solvent was removed
  3. customthe crude product purified by silica column

Sources & evidence

ORD record
ord-9f2279041e904281a7b1b681af73e1b7
Source dataset
uspto-grants-2014_05
Patent number
US08722692B2

Reaction notes

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