Methyl iodide → HCID 53979775, compound

HRID 1604243Notes

Reaction equation

HRID 1604243 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[O:17])[C:5]2[S:10][C:9](=[O:11])[N:8]([CH2:12][CH:13]=[CH:14][CH2:15][CH3:16])[C:6]=2[N:7]=1.[H-].[Na+].I[CH3:21]>CN(C=O)C>[NH2:1][C:2]1[N:3]([CH3:21])[C:4](=[O:17])[C:5]2[S:10][C:9](=[O:11])[N:8]([CH2:12][CH:13]=[CH:14][CH2:15][CH3:16])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 136041167HCID 136041167, compound

Product 1

HCID 53979775HCID 53979775, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-amino-3-(pent-2-ene-1-yl)thiazolo[4,5-d]pyrimidine-2,7(3H,6H)-dione (350 mg, 1.35 mmol), NaH (80% dispersion in mineral oil, 42 mg, 1.4 mmol) and anhydrous DMF (15 mL) was protected from moisture and stirred at ambient temperature for 0.25 h. Iodomethane (0.1 mL, 1.61 mmol) was added and the mixture was stirred for an additional 1 h. The mixture was evaporated in vacuum and then H2O (20 mL) was added. The mixture was stirred for 15 min and then the solid was collected by filtration. The solid was suspended in MeOH (25 mL) and silica gel (5 g) was added. The mixture was evaporated and the dry powder was placed on top of a silica gel column (5.5×20 cm). The column was flash eluted with progressively increasing concentrations of MeOH in CH2Cl2 (%MeOH, vol in L): (0, 1); (1, 1); (2, 1); (3, 1). Eluate containing the homogeneous product was evaporated and the solid was dried in vacuum at 80° C. for 16 h; 240 mg (0.901 mmol, 66%), mp 184-187° C. Ir (KBr): ν3420, 3330 and 3210 (NH2), 1715 (C=O), and 1675 (C=N) cm-1. Uv, λmax (nm), (ε×10-3): pH 1, 300 (9.37), 252 (8.02), 222 (30.9); MeOH, 302 (9.07), 252 (8.35), 222 (31.3); pH 11, 300 (9.41), 252 (8.08), 226 (21.0). 1H nmr (DMSO-d6): δ0.954 (t, 3H, CH3), 2.15-2.22 (m, 2H, CH3CH2), 3.29 (s, 3H, CH3), 4.38 (d, 2H, NCH2), 5.34-5.40 (m, 1H, CHCH) 5.53-5.59 (m, 1H, CHCH), and 7.51 (br s, 2H, NH2). Anal. Calc'd for C11H14N4O2S (266.32): C, 49.61; H, 5.30; N, 21.04. Found: C, 49.93; H, 5.17; N, 20.77.

Workup

  1. stirringthe mixture was stirred for an additional 1 h
  2. customThe mixture was evaporated in vacuum
  3. additionH2O (20 mL) was added
  4. stirringThe mixture was stirred for 15 min
  5. filtrationthe solid was collected by filtration
  6. additionsilica gel (5 g) was added
  7. customThe mixture was evaporated
  8. washeluted
  9. temperaturewith progressively increasing concentrations of MeOH in CH2Cl2 (%MeOH, vol in L)
  10. additionEluate containing the homogeneous product
  11. customwas evaporated
  12. customthe solid was dried in vacuum at 80° C. for 16 h

Sources & evidence

ORD record
ord-2bc374ab0f684c75aa8d73f7250f293d
Source dataset
uspto-grants-1999_11
Patent number
US05994321

Reaction notes

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