Sodium Hydroxide → 153064-93-8

HRID 581223Notes

Reaction equation

HRID 581223 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:15][C@H:14]([OH:16])[C@@H:13]([CH2:17][OH:18])[CH2:12]2)=[C:4](Cl)[N:3]=1.[CH:20]1([NH2:23])[CH2:22][CH2:21]1.[OH-].[Na+]>C(O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:15][C@H:14]([OH:16])[C@@H:13]([CH2:17][OH:18])[CH2:12]2)=[C:4]([NH:23][CH:20]2[CH2:22][CH2:21]2)[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 11108834HCID 11108834, compound

Product 1

HCID 9948407153064-93-8

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(+)-(1S,2R,4R)-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-(hydroxymethyl)cyclopentanol (425 mg, 1.5 mmol), cyclopropylamine (Aldrich, 1.4 mL), and ethanol (4 mL) were refluxed for 3 hours. To the cooled solution was added 1N sodium hydroxide (1.5 mL). The residual oil left on evaporation of volatiles under vacuum was chromatographed on silica gel. Title compound was eluted with methanol:ethyl acetate/15:85 as a white solid foam which solidified to white powder in methanol-acetonitrile (309 mg, 68%); m.p. 174-176° C.; mass spectrum (Cl, CH4) 305 (M+1); 1H-NMR(DMSO-d6)δ: 7.79 (s, 1, H-8); 7.25 (d, J=2.9 Hz, 1, NH), 579 (s, 2, NH2), 4.90-4.75 (m, 1, CH--N), 4.73 (d, J=4.0 Hz, 1, OH), 4.63 (t, J=5.3 Hz, 1, CHOH), 4.08-4.00 (m, 1, CHO), 3.58-3.38 (m, 2, CH2O), 3.05-2.95 (m, 1 CH--NH), 2.35-2.20 (m, 1, CH), 2.18-2.0 (m, 1, 1/2CH2), 2.0-1.9 (m, 2, methylene), 1.7-1.5 (m, 1, 1/2CH2), 0.70-0.50 (m, 4, 2CH2 of cyclopropyl); [α]20589 +7.72°, [α]20546 +8.77°, [α]20436 +14.4°; [α]20365 +20.1° (c=0.66, methanol).

Workup

  1. waitThe residual oil left on evaporation of volatiles under vacuum
  2. customwas chromatographed on silica gel
  3. washTitle compound was eluted with methanol

Sources & evidence

ORD record
ord-ccd376859d264da1a5b76707711aa704
Source dataset
uspto-grants-1999_07
Patent number
US05919941

Reaction notes

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