Sodium Carbonate → 4-Chloro-2-methyl-6-phenyl-pyrimidin-5-ylamine

HRID 2063615Notes

Reaction equation

HRID 2063615 reaction equation
Cl[C:2]1[C:7]([NH2:8])=[C:6]([Cl:9])[N:5]=[C:4]([CH3:10])[N:3]=1.[C:11]1(B(O)O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.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>[Cl:9][C:6]1[C:7]([NH2:8])=[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=[C:4]([CH3:10])[N:5]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 7366744,6-Dichloro-2-methylpyrimidin-5-amine

Product 1

HCID 598466394-Chloro-2-methyl-6-phenyl-pyrimidin-5-ylamine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound was prepared from 4,6-dichloro-2-methyl-pyrimidin-5-ylamine (500 mg, 2.8 mmol), phenylboronic acid (340 mg, 2.8 mmol), sodium carbonate (920 mg, 8.7 mmol, dissolved in minimal amount of water) and Pd(PPh3)4 (160 mg, 0.14 mmol) in 30 mL of glyme by a procedure similar to example 17, step 1 yielding 380 mg (61%) of a solid.

Sources & evidence

ORD record
ord-1b45ae2a448e45cd9bb78b492c176d81
Source dataset
uspto-grants-2012_10
Patent number
US08288398B2

Reaction notes

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