Methylamine → HCID 178482404, compound

HRID 33411Notes

Reaction equation

HRID 33411 reaction equation
Cl[C:2]1[CH:3]2[C:10]([I:11])=[CH:9][N:8]([CH:12]([CH3:14])[CH3:13])[CH:4]2[N:5]=[CH:6][N:7]=1.[CH3:15][NH2:16]>C1COCC1>[I:11][C:10]1[CH:3]2[CH:4]([N:5]=[CH:6][N:7]=[C:2]2[NH:16][CH3:15])[N:8]([CH:12]([CH3:14])[CH3:13])[CH:9]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 597965304-Chloro-7,7a-dihydro-5-iodo-7-isopropyl-4aH-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 178482404HCID 178482404, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-7,7a-dihydro-5-iodo-7-isopropyl-4aH-pyrrolo[2,3-d]pyrimidine (0.3 g, 0.93 mmol) from above was placed within a 15 ml pressure tube. 2 M methylamine in THF (15 ml) was added, and the reaction was left to stir overnight. The volatiles were removed in vacuo, and the residue was dissolved in methanol, 5 ml silica gel were added, and the volatiles were removed in vacuo. The adhered product was purified by silica gel chromatography (ethyl acetate:hexanes), and the requisite fractions were pooled and evaporated in vacuo to yield the desired product (0.25 g, 85% yield). 1H NMR (399.6 MHz, CDCl3) δ 1.43 (6H, d, J=6.8 Hz), 3.13 (3H, d, J=4.8 Hz), 5.0 (1H, sp, J=6.8 Hz), 7.02 (1H, s), 8.35 (1H, s).

Workup

  1. waitthe reaction was left
  2. customThe volatiles were removed in vacuo
  3. dissolutionthe residue was dissolved in methanol
  4. addition5 ml silica gel were added
  5. customthe volatiles were removed in vacuo
  6. customThe adhered product was purified by silica gel chromatography (ethyl acetate:hexanes)
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-c8ab6941816542d796434313a961eab1
Source dataset
uspto-grants-2008_09
Patent number
US07429596B2

Reaction notes

Loading…