HCID 69559439, compound → HCID 9969197, compound

HRID 1796109Notes

Reaction equation

HRID 1796109 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]([C:15]3[N:19]4[CH:20]=[CH:21][C:22]([C:24]([CH3:34])([O:26][Si](CC)(CC)CC)[CH3:25])=[N:23][C:18]4=[N:17][CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]>CCO.Cl>[F:1][C:2]1[CH:3]=[C:4]([C:9]2[N:14]=[C:13]([C:15]3[N:19]4[CH:20]=[CH:21][C:22]([C:24]([OH:26])([CH3:25])[CH3:34])=[N:23][C:18]4=[N:17][CH:16]=3)[CH:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 1

HCID 69559439HCID 69559439, compound

Product 1

HCID 9969197HCID 9969197, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

3-[2-(3,4-Difluorophenyl)pyrimidin-4-yl]-7-(1-methyl-1-triethylsilanyloxyethyl)imidazo[1,2-α]pyrimidine in EtOH (8 ml) was treated with conc. HCl (15 drops) and stirred at room temperature for 12 h. The resulting solid was filtered off and dried under reduced pressure. The resulting solid was added to a mixture of 1N NaOH (30 ml) and CH2Cl2 and stirred vigorously for 5 min. The organics were separated and the aqueous fraction extracted with CH2Cl2 (3×20 ml). The combined organic extracts were dried (MgSO4) and concentrated under reduced pressure to yield 2-{3-[2-(3,4-difluorophenyl)pyrimidin-4-yl]imidazo[1,2-α]pyrimidin-7-yl}propan-2-ol (74 mg, 33%): 1H NMR (400 MHz, d6-DMSO) δ 10.16 (1H, d, J 7.3), 8.90 (1H, d, J 5.5), 8.82 (1H, s), 8.40-8.30 (2H, m), 8.03 (1H, d, J 5.5), 7.73 (1H, d, J 7.3), 7.17-7.08 (1H, m), 7.61 (1H, s), 1.55 (6H, s).

Workup

  1. filtrationThe resulting solid was filtered off
  2. customdried under reduced pressure
  3. additionThe resulting solid was added to a mixture of 1N NaOH (30 ml) and CH2Cl2
  4. stirringstirred vigorously for 5 min
  5. customThe organics were separated
  6. extractionthe aqueous fraction extracted with CH2Cl2 (3×20 ml)
  7. dry with materialThe combined organic extracts were dried (MgSO4)
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ea320fb29f4442cf8307fad17a919d43
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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