Acetic Acid → HCID 69309199, compound

HRID 2117765Notes

Reaction equation

HRID 2117765 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]([C:14]2[N:18]([CH2:19][CH2:20][CH3:21])[C:17]([CH:22]=O)=[N:16][CH:15]=2)[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:24][NH:25][CH3:26].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[NH:1]([C:8]1[N:13]=[C:12]([C:14]2[N:18]([CH2:19][CH2:20][CH3:21])[C:17]([CH2:22][N:25]([CH3:26])[CH3:24])=[N:16][CH:15]=2)[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 674DimethylamineHCID 5003444Sodium cyanoborohydrideHCID 86604212HCID 86604212, compound

Product 1

HCID 69309199HCID 69309199, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-anilino 4-(2-formyl-1-propylimidazol-5-yl)pyrimidine (Method 118; 200 mg, 0.65 mmol) and dimethylamine (391 μl of 2M solution in THF, 0.78 mmol) in MeOH (6 ml) stirred for 3 hours at ambient temperature. Acetic acid (41 mg, 0.716 mmol) and sodium cyanoborohydride (45 mg, 0.716 mmol) were added and the mixture stirred for a further 18 hours. The volatiles were removed by evaporation and residue dissolved in EtOAc (7 ml). This solution was washed with saturated aqueous sodium hydrogen carbonate solution, water, and brine, then dried and the solvent removed by evaporation to give the title compound (210 mg, 96%) as a yellow foam. NMR: 0.62 (t, 6H), 1.50 (m, 2H), 2.23 (s, 6H), 3.60 (s, 2H), 4.56 (m, 2H), 6.98 (t, 1H), 7.10 (d, 1H), 7.28 (t, 2H), 7.62 (m, 3H), 8.39 (d, 1H), 9.39 (s, 1H); m/z 337.

Workup

  1. stirringthe mixture stirred for a further 18 hours
  2. customThe volatiles were removed by evaporation and residue
  3. dissolutiondissolved in EtOAc (7 ml)
  4. washThis solution was washed with saturated aqueous sodium hydrogen carbonate solution, water, and brine
  5. customdried
  6. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-f3f1b0d901754174b39a3edcf419ff3e
Source dataset
uspto-grants-2008_10
Patent number
US07442697B2

Reaction notes

Loading…