Sodium Hydroxide → HCID 88123634, compound

HRID 2352432Notes

Reaction equation

HRID 2352432 reaction equation
[OH-].[Na+].O.[SH:4][C:5]1[N:13]=[CH:12][N:11]=[C:10]2[C:6]=1[NH:7][CH:8]=[N:9]2.Cl[CH2:15][CH:16]([OH:37])[CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:20][CH2:19]1>CN(C=O)C>[OH2:37].[OH:37][CH:16]([CH2:17][N:18]1[CH2:19][CH2:20][N:21]([CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:22][CH2:23]1)[CH2:15][S:4][C:5]1[N:13]=[CH:12][N:11]=[C:10]2[C:6]=1[NH:7][CH:8]=[N:9]2.[OH:37][CH:16]([CH2:17][N:18]1[CH2:19][CH2:20][N:21]([CH:24]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:22][CH2:23]1)[CH2:15][S:4][C:5]1[N:13]=[CH:12][N:11]=[C:10]2[C:6]=1[NH:7][CH:8]=[N:9]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 103601754-(3-Chloro-2-hydroxypropyl)-1-diphenylmethylpiperazineHCID 178527204HCID 178527204, compound

Product 1

HCID 88123634HCID 88123634, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
80 °C

Procedure

To DMF (6 mL), sodium hydroxide pellets (200 mg, 5 mmol) and 6-mercaptopurine monohydrate (0.85 g, 5 mmol) were added. The reaction mixture was stirred and heated to 80° C. for 30 min under nitrogen. The almost clear solution was cooled to room temperature and 1-(1-chloro-2-hydroxy-3-propanyl)-4-(diphenylmethyl)piperazine (1.72 g, 5 mmol) in DMF (10 mL) was added within 5 min. After stirring under nitrogen for 72 h, the mixture was filtered through Celite on a sintered glass funnel and the funnel was rinsed with DMF (2×5 mL). Evaporation of the solvent from the filtrate at 1.0 mm Hg at 50° C. gave a residue which was triturated with 10% methanol/methylene chloride. Filtration removed unreacted 6-mercaptopurine (0.5 g). The solution was purified using flash chromatography on silica gel using 10% methanol/methylene chloride as eluant. The product was isolated by concentration of the desired fractions and purified by trituration with n-pentane to give the title compound (0.35 g, 15.0%), mp 105°-110° C. (dec). DCI/MS M+1 461. 100 MHz 1H NMR (DMSO-d6) δ: 8.6 (s, 1H), 8.18 (s, 1H), 7.2-7.4 (m, 10H), 4.21 (s, 1H) 4.20 (m, 1H), 3.5 (m, 2H), 2.6 (m, 2H), 2.5-2.6 (m, 8H).

Workup

  1. temperatureThe almost clear solution was cooled to room temperature
  2. stirringAfter stirring under nitrogen for 72 h
  3. filtrationthe mixture was filtered through Celite on a sintered glass funnel
  4. washthe funnel was rinsed with DMF (2×5 mL)
  5. customEvaporation of the solvent from the filtrate at 1.0 mm Hg at 50° C.
  6. customgave a residue which
  7. customwas triturated with 10% methanol/methylene chloride
  8. filtrationFiltration
  9. customremoved unreacted 6-mercaptopurine (0.5 g)
  10. customThe solution was purified
  11. customThe product was isolated by concentration of the desired fractions
  12. custompurified by trituration with n-pentane

Sources & evidence

ORD record
ord-db3f316d1138440aa71bd4cc0a6981b5
Source dataset
uspto-grants-1989_10
Patent number
US04876257

Reaction notes

Loading…