1-Propanol, 3-amino-2,2-dimethyl- → 3-{4-[2-(4-Fluorophenyl)-8-isopropoxyimidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamino}-2,2-dimethylpropan-1-ol

HRID 2233115Notes

Reaction equation

HRID 2233115 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([O:16][CH:17]([CH3:19])[CH3:18])=[N:14][CH:13]=[CH:12][N:11]3[C:20]=2[C:21]2[CH:26]=[CH:25][N:24]=[C:23](S(C)(=O)=O)[N:22]=2)=[CH:4][CH:3]=1.[NH2:31][CH2:32][C:33]([CH3:37])([CH3:36])[CH2:34][OH:35]>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([O:16][CH:17]([CH3:19])[CH3:18])=[N:14][CH:13]=[CH:12][N:11]3[C:20]=2[C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:31][CH2:32][C:33]([CH3:37])([CH3:36])[CH2:34][OH:35])[N:22]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 1173261-Propanol, 3-amino-2,2-dimethyl-HCID 588695382-(4-Fluorophenyl)-8-isopropoxy-3-(2-methanesulfonylpyrimidin-4-yl)-imidazo[1,2-a]pyrazine

Product 1

HCID 160504513-{4-[2-(4-Fluorophenyl)-8-isopropoxyimidazo[1,2-a]pyrazin-3-yl]-pyrimidin-2-ylamino}-2,2-dimethylpropan-1-olYield 65.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 2-(4-fluorophenyl)-8-isopropoxy-3-(2-methanesulfonylpyrimidin-4-yl)-imidazo[1,2-a]pyrazine (0.16 g, 0.37 mmol) and 3-amino-2,2-dimethylpropan-1-ol (TCI-US, 0.208 g, 0.74 mmol) in ACN (5 mL) was heated at about 80° C. overnight to give a clear solution. The reaction mixture was cooled to ambient temperature, the volatiles were evaporated, and the resulting residue was dissolved in DCM and washed with water. The organic phase was dried over MgSO4, filtered, and evaporated to give a white solid that was triturated with heptane to afford 0.109 g (64.7%) the title compound as a white solid: LC/MS (Table 1, Method g) Rt=3.01 min; MS m/z: 494.2 (M+H)+.

Workup

  1. customto give a clear solution
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. customthe volatiles were evaporated
  4. dissolutionthe resulting residue was dissolved in DCM
  5. washwashed with water
  6. dry with materialThe organic phase was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give a white solid
  10. customthat was triturated with heptane

Sources & evidence

ORD record
ord-ae0c9fe3293e4b8db6d421c13d94dfb3
Source dataset
uspto-grants-2010_05
Patent number
US07709468B2

Reaction notes

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