Ethanol → 4-(2-Methyl-4-oxo-4H-pyrimido[2,1-b][1,3]benzothiazol-3-yl)benzonitrile

HRID 1642408Notes

Reaction equation

HRID 1642408 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].C([O-])([O-])=O.[Na+].[Na+].C(O)C.FC1C=C([C:29]2[C:34](=[O:35])[N:33]3[CH:36]=[CH:37][S:38][C:32]3=[N:31][C:30]=2[CH3:39])C=C(F)C=1.[C:40]1(C)[CH:45]=CC=[CH:42][CH:41]=1>O>[CH3:39][C:30]1[N:31]=[C:32]2[N:33]([C:34](=[O:35])[C:29]=1[C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)[C:36]1[CH:45]=[CH:40][CH:41]=[CH:42][C:37]=1[S:38]2

Participants

7

Reactant 5

HCID 702EthanolHCID 1140TolueneHCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 667534716-(3,5-Difluorophenyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 667526544-(2-Methyl-4-oxo-4H-pyrimido[2,1-b][1,3]benzothiazol-3-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This compound was prepared from Step 2 intermediate (800 mg, 2.331 mmol), 4-cyanophenylboronic acid (480 mg, 8.271 mmol), Pd[(C6H5)3P]4 (108 mg, 0.093 mmol) and Na2CO3 (1.48 g, 14.023 mol) in a mixture of toluene, ethanol and water according to the procedure described in Intermediate 3, Step 3 to afford the desired product as a light yellow solid; 1H NMR (300 MHz, DMSO-d6) δ 2.49 (s, 3H), 7.53-7.59 (m, 4H), 7.91 (d, J=7.8 Hz, 2H), 8.03-8.10 (m, 1H), 8.80-8.90 (m, 1H); ESI-MS (m/z) 318.30 (M+H)+.

Sources & evidence

ORD record
ord-5517c946c18e4286b130f7b02693f674
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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