Sodium Hydroxide → 153064-93-8

HRID 1684705Notes

Reaction equation

HRID 1684705 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), 5.79 (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]20 578 +7.87°, [α]20546 +8.77°, [α]20436 +14.4°, [α]20365 +20.1°(c=0.65, 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 ethyl acetate/15:85 as a white solid foam which
  4. custom[α]20589 +7.72°, [α]20 578 +7.87°, [α]20546 +8.77°, [α]20436 +14.4°, [α]20365 +20.1°(c=0.65, methanol)

Sources & evidence

ORD record
ord-ae2a06412b0d4b55b08730d083771a73
Source dataset
uspto-grants-1997_06
Patent number
US05641889

Reaction notes

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