2-Methoxyethanol → HCID 23079491, compound

HRID 2197456Notes

Reaction equation

HRID 2197456 reaction equation
[H-].[Na+].Cl[C:4]1[N:12]=[C:11]2[C:7]([NH:8][CH:9]=[N:10]2)=[C:6]([NH2:13])[N:5]=1.[CH3:14][O:15][CH2:16][CH2:17][OH:18]>>[CH3:14][O:15][CH2:16][CH2:17][O:18][C:4]1[N:12]=[C:11]2[C:7]([NH:8][CH:9]=[N:10]2)=[C:6]([NH2:13])[N:5]=1

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydride2×HCID 949042-Chloroadenine2×

Product 1

HCID 23079491HCID 23079491, compound

Procedure

To a flask with 150 ml 2-methoxyethanol, was added NaH (13 g, 60% dispersion in mineral oil). The mixture was allowed to stir at room temperature for 10 min. Then 6-amino-2-chloroadenine (Compound (1)) (25 g, 0.15 mol) was added. The reaction was refluxed for 2 days while monitoring by LC/MS. Additional NaH (5 g, 60% dispersion in mineral oil) was added and refluxing was continued for another day. After the starting material was consumed, the reaction mixture was cooled to rt (“room temperature”) and the solvent was removed under vacuum. Water was added, and the mixture was neutralized with acetic acid until a solid precipitated. The solid Compound (15) was collected and dried under high vacuum. 1H NMR (DMSO-d6) δ 3.28 (s, 3H), δ 3.61 (t, 2H), δ 4.28 (t, 2H), δ 7.08 (bs, 2H), δ 7.88 (s, 1H), δ 145 (bs, 1H); MS: 210.0 (M+H)+, 208.1 (M−1).

Workup

  1. temperatureThe reaction was refluxed for 2 days while monitoring by LC/MS
  2. temperaturerefluxing
  3. waitwas continued for another day
  4. customAfter the starting material was consumed
  5. temperaturethe reaction mixture was cooled to rt (“room temperature”)
  6. customthe solvent was removed under vacuum
  7. additionWater was added
  8. customprecipitated
  9. customThe solid Compound (15) was collected
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-a0da1902a49444ad8989977b34f7cb9f
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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