Sodium Thiosulfate → HCID 86607542, compound

HRID 501181Notes

Reaction equation

HRID 501181 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:21][CH2:20][C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:11]=3[CH2:10]2)=[N:7][CH:8]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[CH:2]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[CH2:21][CH2:20][C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[N:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:11]=3[CH2:10]2)=[N:7][CH:8]=1)=[O:1]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 68461426HCID 68461426, compound

Product 1

HCID 86607542HCID 86607542, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl 2-[5-(hydroxymethyl)pyrimidin-2-yl]-1,2,3,4-tetrahydro-9H-b-carboline-9-carboxylate (2.0 g, 0.0053 moles) in dry DCM (20 mL) was added 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one (2.68 g, 0.0063 moles). After stirring for 5.0 hours, Na2S2O3 (1.0 g), NaHCO3 (1.0 g) in water (15 mL) was added. The two layers were separated. The organic layer was washed with water (20 mL), dried (Na2SO4) and concentrated. The crude product was crystallized using mixture of diethyl ether-hexane to give pure tert-butyl 2-[5-(formyl)pyrimidin-2-yl]-1,2,3,4-tetrahydro-9H-b-carboline-9-carboxylate (1.4 g, 74% yield). Rf=0.4. 1H NMR (DMSO-d6, 400 MHz) ppm: 9.8 (s, 1H, CHO), 8.8 (s, 2H, 2Ar—H), 8.06 (d, 1H, J=8 Hz, 1Ar—H), 7.52 (d, 1H, J=8 Hz, 1Ar—H), 7.33-7.24 (m, 2H, 2Ar—H), 5.32 (s, 2H, CH2), 4.28 (t, 2H, J=8 Hz, CH2), 2.82 (t, 2H, J=8 Hz, CH2), 1.69 (s, 3H, 3CH3); m/e=379 (M+1) (M, 378.425 Calcd. for C21H22N4O3).

Workup

  1. customThe two layers were separated
  2. washThe organic layer was washed with water (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude product was crystallized
  6. additionmixture of diethyl ether-hexane

Sources & evidence

ORD record
ord-0060b589c4d64b94960064b640695978
Source dataset
uspto-grants-2010_08
Patent number
US07772245B2

Reaction notes

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