Dimethyl Sulfone → 2-Amino-5-chloro-3H-pyrimido[4,5-B]indol-4(9H)-one

HRID 2172889Notes

Reaction equation

HRID 2172889 reaction equation
CS(C)(=O)=O.Cl.[C:7](Cl)(=[NH:9])[NH2:8].C([O:13][C:14]([C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][C:23]=2[Cl:25])[NH:18][C:17]=1[NH2:26])=O)C.O.N>C(Cl)(Cl)Cl.O>[NH2:8][C:7]1[NH:9][C:14](=[O:13])[C:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][C:23]=3[Cl:25])[NH:18][C:17]=2[N:26]=1

Participants

7

Reactant 4

HCID 6213Dimethyl SulfoneHCID 3084509Chloroformamidinium chlorideHCID 12896473Azane;hydrateHCID 45103996Ethyl 2-amino-4-chloro-1H-indole-3-carboxylate

Product 1

HCID 1357418862-Amino-5-chloro-3H-pyrimido[4,5-B]indol-4(9H)-oneYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
115 °C

Procedure

Methyl sulfone (1 g) was heated to melting. Compound 7 (106.22 mg, 1.37 mmol) was added and the resulting mixture was stirred and heated at 110-120° C. to dissolve completely. 5 (200 mg, 0.837 mmol) was added in one part to the reaction mixture. Stirring was continued for 30 minutes. About 10 mL water was added to quench the reaction. Ammonia water was added to neutralize the reaction mixture. Solid precipitated out. This solid was filtered. Obtained solid was dissolved in chloroform and methanol, dried (using Na2SO4) and recrystallized. The overall yield was 78%. TLC Rf 0.33 (chloroform-methanol 1:1); mp>250° C.; 1H NMR (DMSO-d6) δ 6.57 (bs, 2H, 2-NH2, exch); 7.04-7.17 (m, 3H, phenyl); 10.41 (s, 1H, 9-NH, exch); 11.64 (s, 1H, 3-NH, exch). Anal. Calculated (C10H7ClN4O. 0.3CH3OH): C, 50.65; H, 3.38; N, 22.94; Cl, 14.52. Found: C, 50.91; H, 3.34; N, 22.60; Cl, 14.77.

Workup

  1. dissolutionto dissolve completely
  2. stirringStirring
  3. customto quench
  4. customthe reaction
  5. customSolid precipitated out
  6. filtrationThis solid was filtered
  7. customObtained solid
  8. dry with materialmethanol, dried (using Na2SO4)
  9. customrecrystallized

Sources & evidence

ORD record
ord-b9c2ee37f7dc42a8b82d44108ce0fe7b
Source dataset
uspto-grants-2015_06
Patent number
US09056869B2

Reaction notes

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