Dimethyl Sulfoxide → HCID 15521617, compound

HRID 1584544Notes

Reaction equation

HRID 1584544 reaction equation
CS(OCC[N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[C:17]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[N:18][C:19]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[N:20][C:9]1=2)(=O)=O.[C-]#N.[Na+].CS(C)=O.S([O-])(=O)(=O)C>O.C(N(CC)CC)C>[N:21]1([C:19]2[N:18]=[C:17]([N:26]3[CH2:27][CH2:28][CH2:29][CH2:30]3)[C:10]3[C:11]4[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=4)[NH:8][C:9]=3[N:20]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 85257MethanesulfonateHCID 537324089-(2-Methanesulfonyloxyethyl)-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole

Product 1

HCID 15521617HCID 15521617, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Procedure

A stirred mixture of 9-[2-(methanesulfonyloxy)ethyl]-2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole (II, EXAMPLE 1 and WO/9626941-A1, 165 g), sodium cyanide (180 g), water (360 mL) and DMSO (3000 mL) are heated at 100° for 18 hr. It is important that the starting mesylate contain traces of triethylamine either left over from its preparation, or added intentionally. The mixture is cooled to 20-25°, diluted with water (approximately 6,000 mL) and filtered. The solid is washed with water to remove excess cyanide, then triturated with acetone. Filtration and drying gives 2,4-di-1-pyrrolidinyl-9H-pyrimido[4,5-b]indole (III), mp 209-211°; NMR (CDCl3) 7.88, 7.22, 7.09, 3.95, 3.67 and 1.98 δ; MS (m/z, FAB, M+H) 308.

Workup

  1. temperatureare heated at 100° for 18 hr
  2. waitleft over from its preparation
  3. additionadded intentionally
  4. temperatureThe mixture is cooled to 20-25°
  5. filtrationfiltered
  6. washThe solid is washed with water
  7. customto remove excess cyanide
  8. customtriturated with acetone
  9. filtrationFiltration
  10. customdrying

Sources & evidence

ORD record
ord-bf9fb396c4aa47caaea73e80ae353b39
Source dataset
uspto-grants-1999_08
Patent number
US05932728

Reaction notes

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