Sodium Carbonate → 1-(4-(4-Chloro-6-morpholino-1,3,5-triazin-2-yl)phenyl)-3-methylurea

HRID 536875Notes

Reaction equation

HRID 536875 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:3]=1.[CH3:15][NH:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23](B2OC(C)(C)C(C)(C)O2)=[CH:22][CH:21]=1)=[O:18].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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:8][C:6]1[N:5]=[C:4]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[N:3]=[C:2]([C:23]2[CH:22]=[CH:21][C:20]([NH:19][C:17]([NH:16][CH3:15])=[O:18])=[CH:25][CH:24]=2)[N:7]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 810762,4-Dichloro-6-morpholino-1,3,5-triazineHCID 177502733-Methyl-1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]urea

Product 1

HCID 866365231-(4-(4-Chloro-6-morpholino-1,3,5-triazin-2-yl)phenyl)-3-methylureaYield 34%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of compound 4-(4,6-dichloro-1,3,5-triazin-2-yl)morpholine (10 g, 42.7 mmol), Pd (PPh3)4 (2.46 g, 2.1 mmol), 1-methyl-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-urea. (11.7 g, 42.4 mmol) and 1N Na2CO3 (168 mL, 168 mmol) in degassed 1,2-dimethoxyethane (400 mL) was heated to 65° C. for 8 hours under N2 atmosphere. The reaction mixture filtered, diluted with water, extracted with ethyl acetate and washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Crude product was purified by silica gel (100-200 mesh) column chromatography using 20-60% ethyl acetate in pet-ether as an eluent. To give 1-(4-(4-chloro-6-morpholino-1,3,5-triazin-2-yl)phenyl)-3-methylurea (5.0 g, 34% yield).

Workup

  1. filtrationThe reaction mixture filtered
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customCrude product was purified by silica gel (100-200 mesh) column chromatography

Sources & evidence

ORD record
ord-d1ed0947096f47ab918f49d59828b784
Source dataset
uspto-grants-2014_10
Patent number
US08859542B2

Reaction notes

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