Hydrogen Sulfide → HCID 86592467, compound

HRID 271276Notes

Reaction equation

HRID 271276 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:4]([C:19]#[N:20])[N:3]=1.[SH2:21].CCN(CC)CC>C(O)(C)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[F:18])=[C:4]([C:19](=[S:21])[NH2:20])[N:3]=1

Participants

5

Reactant 3

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 68575148HCID 68575148, compound

Product 1

HCID 86592467HCID 86592467, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 2-amino-9-(2-fluorobenzyl)-9H-purine-6-carbonitrile (680 mg, 1.85 mmol) in isopropanol (50 mL) was treated with H2S gas for 15 min, then treated with Et3N (0.51 mL, 3.7 mmol), heated at 50° C. for 1 h, concentrated in vacuo, diluted with Et2O and filtered to give the title compound (757 mg, 100%) as a yellow solid; NMR δH (400 MHz, DMSO) 5.36 (2H, s), 6.66 (2H, br s), 7.06-7.43 (4H, m), 8.15 (1H, s), 9.81 (1H, br s) and 10.22 (1H, br s).

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with Et2O
  3. filtrationfiltered

Sources & evidence

ORD record
ord-06c6b37788534b09a97eed32c0544dbb
Source dataset
uspto-grants-2008_11
Patent number
US07452894B2

Reaction notes

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