Hydrochloric Acid → HCID 178507200, compound

HRID 521598Notes

Reaction equation

HRID 521598 reaction equation
I[C:2]1[C:3]([S:12][C:13]2[NH:14][C:15]3[C:20]([N:21]=2)=[C:19]([NH2:22])[N:18]=[CH:17][N:16]=3)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.Cl.[N:24]([O-])=O.[Na+].NC(N)=O>O>[NH2:24][C:2]1[C:3]([S:12][C:13]2[NH:14][C:15]3[C:20]([N:21]=2)=[C:19]([NH2:22])[N:18]=[CH:17][N:16]=3)=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 23668193Sodium NitriteHCID 178508698HCID 178508698, compound

Product 1

HCID 178507200HCID 178507200, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

8-(3-iodonaphthalen-2-ylthio)-9H-purin-6-amine (S13-5). To a suspension of S13-4 (14 mg, 0.0454 mmol) in water (150 μL) at 5° C. was added 6 M HCl (140 μL) over 5 min. Then a solution of NaNO2 (6.3 mg, 0.0908 mmol) in water (70 μL) was added dropwise over 30 min. at below 5° C. The mixture was stirred for an additional 10 min., then urea (1.9 mg, 0.0317 mmol) was added slowly. After 10 minutes, a solution of KI (22.6 mg, 0.136 mmol) in water (70 μL) was added dropwise over 5 min. and the mixture was stirred overnight. The solvent was removed under reduced pressure and the residue was purified by preparatory TLC (CH2Cl2:MeOH—NH3 (7N), 8:1) to give 8 mg (42%) of S13-5 as a solid. 1H NMR (500 MHz, CDCl3/MeOH-d4) δ 8.51 (s, 1H), 8.17 (s, 2H), 7.75-7.80 (m, 2H), 7.52-7.60 (m, 2H); MS (ESI) m/z 420.01 [M+H]+.

Workup

  1. waitAfter 10 minutes
  2. stirringthe mixture was stirred overnight
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by preparatory TLC (CH2Cl2:MeOH—NH3 (7N), 8:1)
  5. customto give 8 mg (42%) of S13-5 as a solid

Sources & evidence

ORD record
ord-760ee71e21244b8faafcc7de3499bb75
Source dataset
uspto-grants-2016_05
Patent number
US09328114B2

Reaction notes

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