Hydrochloric Acid → 4-[1-Azetidin-3-yl-4-(4-fluorophenyl)-1H-imidazol-5-yl]pyrimidin-2-amine

HRID 1896643Notes

Reaction equation

HRID 1896643 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[N:12]([CH:13]3[CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]3)[CH:11]=[N:10][C:9]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)[CH:5]=[CH:4][N:3]=1.Cl>CO>[NH:15]1[CH2:14][CH:13]([N:12]2[C:8]([C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=3)=[C:9]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)[N:10]=[CH:11]2)[CH2:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57461719HCID 57461719, compound

Product 1

HCID 574617124-[1-Azetidin-3-yl-4-(4-fluorophenyl)-1H-imidazol-5-yl]pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl 3-[5-(2-aminopyrimidin-4-yl)-4-(4-fluorophenyl)-1H-imidazol-1-yl]azetidine-1-carboxylate (C4) (2.1 g, 5.1 mmol) in methanol (10 mL) was added aqueous hydrochloric acid (5 N, 30 mL) and the reaction was stirred for 2 hours at room temperature. The solution was concentrated and the residue was diluted with water (100 mL) and ethyl acetate (100 mL). After adjusting the mixture to pH=9 with aqueous ammonia, the aqueous layer was extracted with ethyl acetate (100 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo to give the product as a solid. Yield: 1.1 g, 3.5 mmol, 69%. LCMS m/z 311.4 (M+1). 1H NMR (400 MHz, CD3OD) δ 3.95 (br d, J=7.5 Hz, 4H), 5.51 (m, 1H), 6.38 (br d, J=5.2 Hz, 1H), 7.10 (br dd, J=8.5, 8.5 Hz, 2H), 7.44 (br dd, J=8, 5 Hz, 2H), 8.10 (br d, J=5.0 Hz, 1H), 8.21 (br s, 1H).

Workup

  1. concentrationThe solution was concentrated
  2. additionthe residue was diluted with water (100 mL) and ethyl acetate (100 mL)
  3. extractionthe aqueous layer was extracted with ethyl acetate (100 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-205f20d6e7cd461f8c2fd8cc1b8d894c
Source dataset
uspto-grants-2013_08
Patent number
US08518944B2

Reaction notes

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