Ethanesulfonic acid → HCID 86744926, compound

HRID 1534398Notes

Reaction equation

HRID 1534398 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([Cl:8])[C:5]([NH2:9])=[C:4]([NH:10][C@@H:11]2[CH2:15][C@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]2)[N:3]=1.[CH3:18][C:19](C)(C)C([O-])([O-])[O-].C(S(O)(=O)=O)C>CN(C)C=O>[NH2:1][C:2]1[N:3]=[C:4]2[C:5]([N:9]=[C:18]([CH3:19])[N:10]2[C@@H:11]2[CH2:15][C@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:6]([Cl:8])[N:7]=1

Participants

5

Reactant 3

HCID 11668Ethanesulfonic acidHCID 11459511(1S,4R)-4-[(2,5-Diamino-6-chloro-4-pyrimidinyl)amino]-2-cyclopentene-1-methanolHCID 21927715Trimethylorthoacetate

Product 1

HCID 86744926HCID 86744926, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(±)-cis-4-[(2,5-Diamino-4-chloro-6-pyrimidinyl)amino]-2-cyclopentene-1-methanol prepared as in Example 3 (1.12 g, 4.38 mmol) was stirred in N,N-dimethylformamide (5 mL) with trimethylorthoacetate (30 mL) and ethane sulfonic acid (0.66 g, 5.7 mmol) at 70° C. for 3 days. The resulting solution was evaporated to a yellow syrup. Acetic anhydride (20 mL) was added and this solution was refluxed for 2.5 hours. The resulting dark solution was evaporated to a syrup, which was dissolved in 1N hydrochloric acid (50 mL). After 24 hours, the pH was adjusted to 6 with sodium hydroxide and most of the water evaporated. Crude product was extracted into 20% isopropyl alcohol-chloroform. This solution was dried (MgSO4) and solvent evaporated to leave (±)-cis-4-(2-amino-6-chloro-8-methyl- 9H-purin-9-yl)-2-cyclopentene-1-methanol as a pale yellow glass (0.30 g); structure confirmed by 1H-NMR. This sample was dissolved in methanol (10 mL) and stirred in a Parr bomb with cyclopropylamine (1 mL) at 70° C. for 12 hours. Evaporation and chromatography on silica gel gave title compound, eluted as a cream-colored solid foam (136 mg) with 5% methanol-chloroform.

Workup

  1. customThe resulting solution was evaporated to a yellow syrup
  2. additionAcetic anhydride (20 mL) was added
  3. temperaturethis solution was refluxed for 2.5 hours
  4. customThe resulting dark solution was evaporated to a syrup, which
  5. dissolutionwas dissolved in 1N hydrochloric acid (50 mL)
  6. customevaporated
  7. extractionCrude product was extracted into 20% isopropyl alcohol-chloroform
  8. dry with materialThis solution was dried (MgSO4) and solvent
  9. customevaporated

Sources & evidence

ORD record
ord-614ea80ac0514817ae47c3b6456de548
Source dataset
uspto-grants-1992_02
Patent number
US05089500

Reaction notes

Loading…