Triethylamine → HCID 67812514, compound

HRID 728663Notes

Reaction equation

HRID 728663 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]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:4](Cl)[N:3]=1.[NH2:19][CH2:20][CH:21]([OH:24])[CH2:22][OH:23].C(N(CC)CC)C.COC(O)C.[OH-].[Na+]>>[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]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:4]([NH:19][CH2:20][CH:21]([OH:24])[CH2:22][OH:23])[N:3]=1

Participants

6

Reactant 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 735613-Amino-1,2-propanediolHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-HCID 30156371-Methoxyethanol

Product 1

HCID 67812514HCID 67812514, compound

Procedure

A solution of (±)-cis-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol from Example 4 (0.544, 2 mmol), 3-amino-1,2-propanediol (1.87 mg, 2 mmol), triethylamine (607 mg, 6 mmol) and methoxyethanol (6 ml) were refluxed overnight under nitrogen. 1 N NaOH (2 ml) was added and the solution was concentrated under vacuum and dried by evaporation of ethanol. The residual oil was chromatographed on silica gel. Title compound was eluted with 20% methanol-chloroform; white powder after crystallization from acetonitrile-methanol (0.300 g, 47%), m.p. 119-121° C. 1H-NMR: (DMSO-d6) δ 7.60 (s, 1, H-8), 6.90-6.80 (br m, 1, NH), 6.10 (m, 1, =CH), 5.85 (m, 3, =CH and NH2), 5.40 (br m, 1, CH--N), 4.90 (m, 1, OH), 4.72 (t, J=5.3,1, OH), 4.62 (t, J=5.9, 1, OH), CH), 2.70-2.50 (m, overlapping solvent, 0.5 CH2), 1.70-1.50 (m, 1, 0.5 CH2).

Workup

  1. concentrationthe solution was concentrated under vacuum
  2. dry with materialdried by evaporation of ethanol
  3. customThe residual oil was chromatographed on silica gel
  4. washTitle compound was eluted with 20% methanol-chloroform
  5. customwhite powder after crystallization from acetonitrile-methanol (0.300 g, 47%), m.p. 119-121° C

Sources & evidence

ORD record
ord-02405259c1d64b8c89bdaeb04cbb3fe9
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Reaction notes

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