Hydrochloric Acid → N-(3-dimethylaminomethyl-phenyl)-N'-methyl-pyrimidine-4,6-diamine

HRID 1038713Notes

Reaction equation

HRID 1038713 reaction equation
ClC1C(OC)=CC=C(Cl)C=1NC(=O)[N:13]([CH3:34])[C:14]1[CH:19]=[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24](N3CCN(C)CC3)=[CH:23][CH:22]=2)[N:17]=[CH:16][N:15]=1.[CH3:36][N:37]([CH2:39]C1C=C(N)C=CC=1)[CH3:38].Cl>O1CCOCC1>[CH3:36][N:37]([CH2:39][C:25]1[CH:26]=[C:21]([NH:20][C:18]2[CH:19]=[C:14]([NH:13][CH3:34])[N:15]=[CH:16][N:17]=2)[CH:22]=[CH:23][CH:24]=1)[CH3:38]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 992943-amino-N,N-dimethylbenzylamineHCID 565947453-(2,6-Dichloro-3-methoxy-phenyl)-1-methyl-1-(6-[4-(4-methyl-piperazin-1-yl)-phenylamino]-pyrimidin-4-yl)-urea

Product 1

HCID 66669947N-(3-dimethylaminomethyl-phenyl)-N'-methyl-pyrimidine-4,6-diamineYield 59.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of (6-chloro-pyrimidin-4-yl)-methyl-amine (Example 1) (750 mg, 5.2 mmol), 3-dimethylaminomethyl-phenylamine (787 mg, 5.2 mmol) and 4N HCl in dioxane (15 ml) is heated in a sealed tube to 150° C. for 5 h. The reaction mixture is concentrated, diluted with DCM and a saturated aqueous solution of sodium bicarbonate. The aqueous layer is separated and extracted with DCM. The organic phase is washed with brine, dried (sodium sulfate), filtered and concentrated. Purification of the residue by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1) affords 800 mg of the title compound as a white solid: ESI-MS: 258.1 [MH]+; tR=1.00 min (purity: 100%, gradient J); TLC: Rf=0.14 (DCM/MeOH+1% NH3aq, 9:1).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. additiondiluted with DCM
  3. customThe aqueous layer is separated
  4. extractionextracted with DCM
  5. washThe organic phase is washed with brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the residue by silica gel column chromatography (DCM/MeOH+1% NH3aq, 9:1)

Sources & evidence

ORD record
ord-a19e0b18adb94208bef9924b496ac1fa
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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