1,3-Propanediol → 3-(2-(Dimethylamino)-5-pyrimidyl)aniline

HRID 1075455Notes

Reaction equation

HRID 1075455 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]([CH3:10])[CH3:9])=[N:6][CH:7]=1.[NH2:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].C(O)CCO>O.C(COC)OC.C(OCC)(=O)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>[CH3:9][N:8]([CH3:10])[C:5]1[N:4]=[CH:3][C:2]([C:16]2[CH:17]=[C:12]([CH:13]=[CH:14][CH:15]=2)[NH2:11])=[CH:7][N:6]=1

Participants

9

Reactant 4

HCID 104421,3-PropanediolHCID 11430Potassium CarbonateHCID 922693-Aminophenylboronic acidHCID 127353155-Bromo-N,N-dimethylpyrimidin-2-amine

Product 1

HCID 538349803-(2-(Dimethylamino)-5-pyrimidyl)anilineYield 74%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-2-(dimethylamino)pyrimidine (6.76g, 33.17mmol), 3-aminophenylboronic acid hemisultat (7.4g, 39.78mmol) potassium carbonate (13.73g, 99.49mmol), 1,3-propanediol (12ml, 166mmol) and tetrakis(triphenylphosphine)palladium(0) (0.2g) in a mixture of water (30ml) and dimethoxyethane (60ml) is heated to 80° C. under nitrogen overnight. After cooling the mixture is diluted with water and ethyl acetate and is filtered through a fluted filterpaper. The layers are separated and the aqeous phase is extracted once with ethyl acetate. The combined organic phases are dried over sodium sulfate and evaporated to dryness. The residue is triturated with a mixture of ethyl acetate and petroleum ether (1:1) to leave crystalline 2h (5.26g, 74%). Mp 115.5-117° C.

Workup

  1. temperatureAfter cooling the mixture
  2. filtrationis filtered through a fluted filterpaper
  3. customThe layers are separated
  4. extractionthe aqeous phase is extracted once with ethyl acetate
  5. dry with materialThe combined organic phases are dried over sodium sulfate
  6. customevaporated to dryness
  7. customThe residue is triturated with a mixture of ethyl acetate and petroleum ether (1:1)

Sources & evidence

ORD record
ord-7570d669382c40e982bb85241a1119a2
Source dataset
uspto-grants-1999_05
Patent number
US05902813

Reaction notes

Loading…