Sodium Hydroxide → HCID 57133849, compound

HRID 1684706Notes

Reaction equation

HRID 1684706 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[CH2:24][CH2:23][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]([N:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[N:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 11108834HCID 11108834, compound

Product 1

HCID 57133849HCID 57133849, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(+)-(1S, 2R, 4R)-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-(hydroxymethyl)cyclopentanol (426 mg 1.5 mmol), pyrrolidine (99%, Aldrich, 1.26 mL), and ethanol (8 mL) were refluxed for 20 minutes. To the cooled solution was added 1N sodium hydroxide (1.5 mL). Volatiles were evaporated and the residue chromatographed on silica gel. Title compound was eluted with 12% methanol-chloroform as a white solid foam which solidified from 95% ethanol to white powder (324 mg, 64% ); mp 114°-117°; mass spectrum (Cl, CH4): 319(M+1); 1H-NMR (DMSO-d6)δ: 7.81 (s, 1, H-8), 5.76 (br s, 2, NH2), 5.0-4.8 (m, 1, CHN), 4.76(d, J=4.1 Hz, 1, OH), 4.66 (t, J=5.2 Hz, 1, CH2OH), 4.15-4.0 (m, overlapping br m at 4.1-3.4 and m at 3.6-3.35, total 7, CHO, 2CH2N and CH2O), 2.4-2.2 (m, 1, 1/2CH2), 2.2-1.8 (m, 7,methylenes), 1.7-1.5(m, 1, 1/2CH2); [α]20589 +10.5°, [α]20578 +11.00°, [α]20546 +12.4°, [α]20436 +19.5°, [α]20365 +25.5°(c=1.43, methanol).

Workup

  1. customVolatiles were evaporated
  2. customthe residue chromatographed on silica gel
  3. washTitle compound was eluted with 12% methanol-chloroform as a white solid foam which

Sources & evidence

ORD record
ord-94e84c0420fd4993b76617d2bcd328e4
Source dataset
uspto-grants-1997_06
Patent number
US05641889

Reaction notes

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