Ammonia → HCID 53717526, compound

HRID 343563Notes

Reaction equation

HRID 343563 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:22]#[C:23][C:24]4[CH:29]=[CH:28][N:27]=[C:26](S(C)(=O)=O)[N:25]=4)[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH3:34]>CO>[NH2:34][C:26]1[N:25]=[C:24]([C:23]#[C:22][C:15]2([C:9]3[CH:10]=[CH:11][C:12]([O:13][CH3:14])=[C:7]([O:6][CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[CH:8]=3)[CH2:20][CH2:19][C:18](=[O:21])[CH2:17][CH2:16]2)[CH:29]=[CH:28][N:27]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 54364783HCID 54364783, compound

Product 1

HCID 53717526HCID 53717526, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(2-methylsulfonylpyrimidin-4-ylethynyl)cyclohexan-1-one (0.26 g, 0.56 mmol) in methanol (4 mL) at -78° C. was condensed liquid ammonia (4 mL), the pressure tube was sealed and the reaction was stirred at room temperature for 2.5 h. After cooling, the solvents were evaporated. Purification required two flash chromatographies, eluting first with 2:98 methanol:dichloromethane and secondly with 4:6 ethyl acetate:hexanes, to provide 4-(2-aminopyrimidin-4-ylethynyl)-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one as a white solid (0.18 g, 73%), mp 68°-70° C. Anal. (C24H27N3O3.0.2 H2O) calcd: C, 70.46; H, 6.75; N, 10.27; found: C, 70.73; H, 6.79; N, 9.87.

Workup

  1. customat -78° C.
  2. customthe pressure tube was sealed
  3. temperatureAfter cooling
  4. customthe solvents were evaporated
  5. customPurification
  6. washeluting first with 2:98 methanol

Sources & evidence

ORD record
ord-bace6b8be079405dbfd5fdd78af24440
Source dataset
uspto-grants-1999_01
Patent number
US05861421

Reaction notes

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