Potassium Carbonate → HCID 16129033, compound

HRID 1870056Notes

Reaction equation

HRID 1870056 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[N:11][C:12]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([O:22][C:23]([N:25]4[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]4)=[O:24])=[CH:18][CH:17]=3)=[N:13][CH:14]=2)=[CH:5][CH:4]=1.NC1C=CC(OC(N2CCN(C)CC2)=O)=CC=1.COC1C=CC(B(O)O)=CC=1.C([O-])([O-])=O.[K+].[K+]>ClCCl.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.COCCOC>[NH4+:11].[OH-:2].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[N:13][C:12]([NH:15][C:16]3[CH:17]=[CH:18][C:19]([O:22][C:23]([N:25]4[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]4)=[O:24])=[CH:20][CH:21]=3)=[N:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

10

Reactant 4

HCID 11430Potassium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 16129033HCID 16129033, compoundHCID 57632862HCID 57632862, compound

Product 2

HCID 14923Ammonium HydroxideHCID 16129033HCID 16129033, compoundYield 86%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

4-Methyl-piperazine-1-carboxylic acid 4-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-phenyl ester can be synthesized by the following procedure. A suspension of 4-methyl-piperazine-1-carboxylic acid 4-amino-phenyl ester (0.166 mmol) (from example 31), 4-methoxy phenyl boronic acid (0.199 mmol), K2CO3 (0.36 mmol) and Pd(PPh3)4 (0.0166 mmol) in a 5:1 mixture of DME:H2O (1.5 mL) is heated at 80° C. for 10 min. The reaction mixture is cooled to rt, diluted with dichloromethane, washed with NH4Cl, and dried under reduced pressure. The crude is purified by a short silica column using a mixture 9.5:0.5:0.1=DCM:MeOH:NH4OH to afford 4-methyl-piperazine-1-carboxylic acid 4-[5-(4-methoxy-phenyl)-pyrimidin-2-ylamino]-phenyl ester as white powder (86%). 1H NMR (400 MHz, CDCl3) δ 8.53 (s, 2H), 7.57 (d, J=8.0 Hz, 2H), 7.37 (d, J=8.0 Hz, 2H), 7.12 (b.s, 1H), 7.0.2 (m, 2H), 6.95 (m, 2H), 3.79 (s, 3H), 3.71-3.69 (m, 4H), 2.51-2.50 (m, 4H). MS (m/z) (M+1)+ 420.2.

Workup

  1. washwashed with NH4Cl
  2. customdried under reduced pressure
  3. customThe crude is purified by a short silica column

Sources & evidence

ORD record
ord-ee9366c34af342e89a93a26aedb877fb
Source dataset
uspto-grants-2009_12
Patent number
US07638523B2

Reaction notes

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