Azetidine → HCID 57159919, compound

HRID 581225Notes

Reaction equation

HRID 581225 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.[NH:20]1[CH2:23][CH2:22][CH2:21]1.[OH-].[Na+]>CO>[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]([N:20]2[CH2:23][CH2:22][CH2:21]2)[N:3]=1

Participants

5

Reactant 3

HCID 10422AzetidineHCID 14798Sodium HydroxideHCID 11108834HCID 11108834, compound

Product 1

HCID 57159919HCID 57159919, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(+)-(1S,2R,4R)-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-(hydroxymethyl)cyclopentanol (340 mg, 1.20 mmol) and azetidine (98%, Aldrich, 1.0 mL) and methanol (6 mL) were maintained at 60° C. in a sealed tube for 18 hours. To the cooled solution was added 1N sodium hydroxide (1.2 mL). Volatiles were evaporated and the residue chromatographed on silica gel. Title compound was eluted with methanol:ethyl acetate/15:85 as a white foam which solidified to white powder from methanol-acetonitrile (333 mg, 91%), mp 194-195°; mass spectrum (Cl, CH4) 305 (M+1); 1H-NMR (DMSO-d6)δ: 7.81 (s, 1, H8), 5.88 (br s, 2, NH2), 495-4.80 (m, 1, CH--N), 4.76 (d, J=3.9 Hz, 1, OH), 4.66 (t, J=5.0 Hz, 1, CH2 --OH), 4.4-4.15(br m, 4, 2CH2N), 4.10-4.0 (m, 1, CHO), 3.6-3.4 (m, 2, CH2O), 2.5-1.9 (m, 6, methylene), 1.75-1.5((m, 1, 1/2CH2); [α]20589 +10.1°, [α]20578 +10.7°, [α]20540 +11.9°, [α]20436 +18.3°, [α]20365 +25.2° (c=0.812, methanol).

Workup

  1. customVolatiles were evaporated
  2. customthe residue chromatographed on silica gel
  3. washTitle compound was eluted with methanol
  4. custom[α]20589 +10.1°, [α]20578 +10.7°, [α]20540 +11.9°, [α]20436 +18.3°, [α]20365 +25.2° (c=0.812, methanol)

Sources & evidence

ORD record
ord-57e13847c8f1445db7951da98c26bae9
Source dataset
uspto-grants-1999_07
Patent number
US05919941

Reaction notes

Loading…