Sodium Carbonate → HCID 66752909, compound

HRID 1642385Notes

Reaction equation

HRID 1642385 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[S:19][CH:18]=[CH:17][N:5]2[C:6](=[O:16])[C:7]=1[C:8]1[CH:15]=[CH:14][C:11](C#N)=[CH:10][CH:9]=1.[CH3:20][O:21]C1C=CC(B(O)O)=CC=1.C(=O)([O-])[O-].[Na+].[Na+].FC1C=C(C2C(=O)N3C=CSC3=NC=2C)C=C(F)C=1>C1(C)C=CC=CC=1.O.C(O)C>[CH3:20][O:21][C:11]1[CH:14]=[CH:15][C:8]([C:7]2[C:6](=[O:16])[N:5]3[CH:17]=[CH:18][S:19][C:4]3=[N:3][C:2]=2[CH3:1])=[CH:9][CH:10]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 66752927HCID 66752927, compoundHCID 667534716-(3,5-Difluorophenyl)-7-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 66752909HCID 66752909, compoundYield 78.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

The title compound was prepared by coupling reaction of Step 2 intermediate from Intermediate 4 (6.8 g, 23.271 mmol) with 4-methoxyphenylboronic acid (4.95 g, 32.490 mmol) in the presence of Pd[(C6H5)3P]4 (1.076 g, 0.931 mmol) and sodium carbonate (14.812 g, 139.071 mmol) in a mixture of toluene, ethanol and water according to the procedure described in Intermediate 3, step 3 yielded 5.0 g of the desired compound as an off-white solid; 1H NMR (300 MHz, DMSO-d6) δ 2.29 (s, 3H), 3.83 (s, 3H), 6.92-6.96 (m, 3H), 7.20-7.23 (m, 2H), 7.94 (d, J=4.8 Hz, 1H); ESI-MS (m/z) 273.51 (M+H)+.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-e753ff3e2cfb4c418111b79b98deeb51
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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