Chloroacetaldehyde → 7-[2-(6-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-8-propyl-imidazo[1,2-c]pyrimidine

HRID 916640Notes

Reaction equation

HRID 916640 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8][N:9]2[CH:13]=[CH:12][N:11]=[C:10]2[C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[N:15]=2)[C:3]=1[CH2:21][CH2:22][CH3:23].Cl[CH2:25][CH:26]=O>CN(C=O)C>[F:20][C:16]1[N:15]=[C:14]([C:10]2[N:9]([CH2:8][C:4]3[N:5]=[CH:6][N:7]4[CH:25]=[CH:26][N:1]=[C:2]4[C:3]=3[CH2:21][CH2:22][CH3:23])[CH:13]=[CH:12][N:11]=2)[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 117230296-Amino-4-[2-(6-fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-5-propyl-pyrimidine

Product 1

HCID 112329787-[2-(6-Fluoro-pyridin-2-yl)-imidazol-1-ylmethyl]-8-propyl-imidazo[1,2-c]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 105 (1.2 mmol) and chloroacetaldehyde (1 mL) in DMF (10 ml) is heated overnight at 70° C. in a sealed tube. The solvent is removed in vacuo and EtOAc (15 ml) and water (15 ml) are added to the residue. The layers are separated and the aqueous layer is extracted with EtOAc (15 ml). The combined extracts are washed with brine (15 ml), dried (Na2SO4) and evaporated. PTLC separation of the residue with 10% MeOH in CH2Cl2 provides the title compound as a white solid (106). 1H-NMR (CDCl3) δ: 8.78 (s, 1H), 8.11 (dd, 1H), 7.83 (q, 1H), 7.65 (d, 1H), 7.56 (d, 1H), 7.18 (d, 1H), 7.15 (d, 1H), 6.83 (dd, 1H), 6.04 (s, 2H), 3.07–3.13 (m, 2H), 1.62–1.72 (m, 2H), 0.99 (t, 3H).

Workup

  1. customThe solvent is removed in vacuo and EtOAc (15 ml) and water (15 ml)
  2. additionare added to the residue
  3. customThe layers are separated
  4. extractionthe aqueous layer is extracted with EtOAc (15 ml)
  5. washThe combined extracts are washed with brine (15 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customPTLC separation of the residue with 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-c09e257dab06453495e2cfbdcc86d8b6
Source dataset
uspto-grants-2007_09
Patent number
US07271170B2

Reaction notes

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