2-[2,4-Di(pyrrolidin-1-yl)-5,6,7,8-tetrahydro-9H-pyrimido[4,5-b]indol-9-yl]ethan-1-ol → 2-[2,4-Di(pyrrolidin-1-yl)-9H-pyrimido[4,5-b]indol-9-yl]ethan-1-ol

HRID 482318Notes

Reaction equation

HRID 482318 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6]2[C:13]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[N:14][C:15]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[N:16][C:5]1=2>[Pd].C1C2C(CCCC2)CCC1.C(Cl)Cl>[OH:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]2[C:13]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[N:14][C:15]([N:17]3[CH2:21][CH2:20][CH2:19][CH2:18]3)=[N:16][C:5]1=2

Participants

5

Reactant 1

HCID 155216152-[2,4-Di(pyrrolidin-1-yl)-5,6,7,8-tetrahydro-9H-pyrimido[4,5-b]indol-9-yl]ethan-1-ol

Product 1

HCID 155216162-[2,4-Di(pyrrolidin-1-yl)-9H-pyrimido[4,5-b]indol-9-yl]ethan-1-ol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 7044DecalinSolvent

Procedure

A mixture of 9-(2-hydroxyethyl)-2,4-di-1-pyrrolidinyl-5,6,7,8-tetrahydro-9H-pyrimido[4,5-b]indole (VII, EXAMPLE2, 5.14 g) and palladium on carbon (10%, 1.4 g) in decalin (250 mL) is heated at reflux for 3 hr. The mixture is cooled to 20°-25°, diluted with methylene chloride (250 mL) and filtered through diatomaceous earth. Removal of the solvent from the filtrate, followed by chromatography (silica gel, 1% methanol/chloroform) of the resulting residue gives the title compound, mp=110°-111; MS (m/z) 351, 323, 307, 296 and 279; NMR (CDCl3) 7.89, 7.23, 7.13, 6.97, 4.38, 4.05, 3.92, 3.62 and 2.0-1.9 δ.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 hr
  3. temperatureThe mixture is cooled to 20°-25°
  4. filtrationfiltered through diatomaceous earth
  5. customRemoval of the solvent from the filtrate

Sources & evidence

ORD record
ord-7e89f14f87f54e839d755c5beb2b104a
Source dataset
uspto-grants-1998_08
Patent number
US05795986

Reaction notes

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