Azetidine → HCID 57159919, compound

HRID 357714Notes

Reaction equation

HRID 357714 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 acetatel 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]20356 +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]20356 +25.2°(c=0.812, methanol)

Sources & evidence

ORD record
ord-a81fe43e52a94e12b16fd766a8538bb4
Source dataset
uspto-grants-1998_11
Patent number
US05840990

Reaction notes

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