Diglycolamine → HCID 131723467, compound

HRID 2305996Notes

Reaction equation

HRID 2305996 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)[C:5]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][CH:17]=2)=[CH:4][N:3]=1.NCCOCCO>CC(O)C.Cl>[CH3:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][C:5]2[C:6]([N:8]3[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]3)=[N:7][CH:2]=[N:3][CH:4]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 13578DiglycolamineHCID 18432574HCID 18432574, compound

Product 1

HCID 131723467HCID 131723467, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3776IsopropanolSolvent2×

Procedure

A solution of 2-chloro-5-(4-methylbenzyl)-4-(4-methylpiperazino)pyrimidine (1.46 g, cc mmoles), 2-propanol (25 mL) and 2-(2-aminoethoxy)ethanol (4.79 g, 46 mmoles) was heated in a stainless steel reaction vessel at 155° C. for 16 hours. The vessel contents were spin evaporated in vacuo at 60° C. to give a residue that was partitioned between dichloromethane (35 mL) and water (150 mL). The dichloromethane phase was separated and washed with water (150 mL), and finally with brine (100 mL). The solution was dried over sodium sulfate, filtered, and spin evaporated in vacuo to give a syrup. The syrup was dissolved in 2-propanol (20 mL), 37% hydrochloric acid (15 drops) was added, and the solution was spin evaporated in vacuo. The residue was crystallized from methanol (2 mL) to give 0.34 g of 2-(2-hydroxyethoxy)ethylamino)-5-(4-methylbenzyl)-4-(4-methylpiperazino)pyrimidine as carmel colored crystals, mp 207-209° C.

Workup

  1. customThe vessel contents were spin evaporated in vacuo at 60° C.
  2. customto give a residue that
  3. customwas partitioned between dichloromethane (35 mL) and water (150 mL)
  4. customThe dichloromethane phase was separated
  5. washwashed with water (150 mL)
  6. dry with materialThe solution was dried over sodium sulfate
  7. filtrationfiltered
  8. customspin evaporated in vacuo
  9. customto give a syrup
  10. customevaporated in vacuo
  11. customThe residue was crystallized from methanol (2 mL)

Sources & evidence

ORD record
ord-b3b2bd9bc59c447cb8aa3cfb009a8c8d
Source dataset
uspto-grants-2002_08
Patent number
US06440965B1

Reaction notes

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