Methanol → 5-Morpholin-4-yl-2-phenyl-imidazo[1,2-c]pyrimidin-7-ylamine

HRID 908217Notes

Reaction equation

HRID 908217 reaction equation
[N:1]1([C:7]2[N:12]=[C:11]([NH2:13])[CH:10]=[C:9]([NH2:14])[N:8]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.Br[CH2:16][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=O.C([O-])(O)=O.[Na+].CO>O>[N:1]1([C:7]2[N:8]3[CH:16]=[C:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[N:14]=[C:9]3[CH:10]=[C:11]([NH2:13])[N:12]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6259Phenacyl bromideHCID 516892Sodium BicarbonateHCID 143394012-(Morpholin-4-yl)pyrimidine-4,6-diamine

Product 1

HCID 670419775-Morpholin-4-yl-2-phenyl-imidazo[1,2-c]pyrimidin-7-ylamineYield 59.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-morpholin-4-yl-pyrimidine-4,6-diamine (1.0 g, 5.1 mmol), ω-bromoacetophenone (1.02 g, 5.1 mmol), NaHCO3 (473 mg, 6 mmol) and methanol (15 ml) was heated under an atmosphere of argon to reflux (3 h). After cooling, water (10 ml) was added (the gummy precipitate could not be isolated). Methanol was evaporated, the residue was taken up in ethyl acetate, washed (water), and dried (Na2SO4). The solvent was evaporated and the title compound (900 mg, 50%) was isolated from the mixture by column chromatography (silica gel, heptane:ethyl acetate=80:20-60:40). MS (m/e)=296.3 [M+H+].

Workup

  1. temperaturewas heated under an atmosphere of argon
  2. temperatureto reflux (3 h)
  3. temperatureAfter cooling
  4. custombe isolated)
  5. customMethanol was evaporated
  6. washwashed (water)
  7. dry with materialdried (Na2SO4)
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-3bb71263ecd84ccfb137453f7b2c5b68
Source dataset
uspto-grants-2011_09
Patent number
US08017604B2

Reaction notes

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