Hydrochloric Acid → 2-[4-(Piperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine

HRID 1441307Notes

Reaction equation

HRID 1441307 reaction equation
C([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:31]=[CH:30][C:13]([NH:14][C:15]3[N:20]=[C:19]([C:21]4[N:25]([CH:26]([CH3:28])[CH3:27])[C:24]([CH3:29])=[N:23][CH:22]=4)[CH:18]=[CH:17][N:16]=3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=O)C.Cl>C(O)(C)C>[N:7]1([C:10]2[CH:31]=[CH:30][C:13]([NH:14][C:15]3[N:20]=[C:19]([C:21]4[N:25]([CH:26]([CH3:28])[CH3:27])[C:24]([CH3:29])=[N:23][CH:22]=4)[CH:18]=[CH:17][N:16]=3)=[CH:12][CH:11]=2)[CH2:8][CH2:9][NH:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 113160942-[4-(4-Acetylpiperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine

Product 1

HCID 686857662-[4-(Piperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2-[4-(4-Acetylpiperazin-1-yl)anilino]-4-(1-isopropyl-2-methyl-1H-imidazol-5-yl)pyrimidine (Example 18; 1.3 g) was stirred and heated in isopropanol (15 ml) and 33% hydrochloric acid (1.5 ml) at 90° C. for 4.5 hours. The reaction was evaporated under reduced pressure and then basified with 7N ammonia in MeOH and re-evaporated. Toluene was added and the mixture was re-evaporated (3 times). The residue was purified by chromatography on neutral alumina, activity II eluting with MeOH:DCM (5:95) to give the title compound as a yellow gum. (330 mg 28%). NMR: 1.40 (d, 6H), 2.46 (s, 3H), 2.82 (m, 4H), 2.96 (m, 4H), 5.69 (septuplet, 1H), 6.85 (d, 2H), 6.93 (d, 1H), 7.18 (s, 1H), 7.42 (d, 2H), 8.30 (d, 1H), 9.11 (s, 1H); m/z 378.

Workup

  1. customThe reaction was evaporated under reduced pressure
  2. customre-evaporated
  3. additionToluene was added
  4. customthe mixture was re-evaporated (3 times)
  5. customThe residue was purified by chromatography on neutral alumina, activity II
  6. washeluting with MeOH:DCM (5:95)

Sources & evidence

ORD record
ord-dd43d9c31d1348ff9ecc01b4d8f2ae62
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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