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

HRID 482317Notes

Reaction equation

HRID 482317 reaction equation
[N:1]1([C:6]2[N:11]=[C:10]([NH:12][CH2:13][CH2:14][OH:15])[CH:9]=[C:8]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C:23]1=O.C(N(CC)C(C)C)(C)C>C(#N)C>[OH:15][CH2:14][CH2:13][N:12]1[C:23]2[CH2:24][CH2:25][CH2:26][CH2:27][C:22]=2[C:9]2[C:8]([N:16]3[CH2:17][CH2:18][CH2:19][CH2:20]3)=[N:7][C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)=[N:11][C:10]1=2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 117897582-BromocyclohexanoneHCID 155216142-{[2,6-Di(pyrrolidin-1-yl)pyrimidin-4-yl]amino}ethan-1-ol

Product 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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-[(2,6-di-(1-pyrrolidinyl)pyrimidin-4-yl)amino]ethanol (VI, Example1, 5.55 g), 2-bromocyclohexanone (3.54 g), N,N-diisopropylethylamine (2.65 g) and acetonitrile (60 mL) is heated at reflux for 44 hr. The reaction mixture is cooled to 20°-25° and concentrated under reduced pressure. The residue is partitioned between methylene chloride and aqueous sodium bicarbonate solution. The organic phase is dried over sodium sulfate, filtered, and concentrated. Chromatography (silica gel, 2.5% acetone/chloroform) gives the title compound, NMR (CDCl3) 7.64, 4.05, 3.91, 3.67, 3.55, 2.72, 2.56, 2.0-1.7 δ; MS (m/z) calc'd=355.2372, found=355.2368.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 44 hr
  3. temperatureThe reaction mixture is cooled to 20°-25°
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is partitioned between methylene chloride and aqueous sodium bicarbonate solution
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-dbe6ad201fdf40d48eb98e37bf6ba6fd
Source dataset
uspto-grants-1998_08
Patent number
US05795986

Reaction notes

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