Hydrogen Sulfide → HCID 3006458, compound

HRID 1073104Notes

Reaction equation

HRID 1073104 reaction equation
[SH2:1].O(C)[Na].[NH2:5][C:6]1[C:7]2[C:14]([C:15]#[N:16])=[CH:13][N:12]([CH2:17][O:18][CH:19]([CH2:22][OH:23])[CH2:20][OH:21])[C:8]=2[N:9]=[CH:10][N:11]=1>>[NH2:5][C:6]1[C:7]2[C:14]([C:15](=[S:1])[NH2:16])=[CH:13][N:12]([CH2:17][O:18][CH:19]([CH2:20][OH:21])[CH2:22][OH:23])[C:8]=2[N:9]=[CH:10][N:11]=1

Participants

4

Reactant 3

HCID 402Hydrogen SulfideHCID 4524827H-Pyrrolo(2,3-d)pyrimidine-5-carbonitrile, 4-amino-7-((2-hydroxy-1-(hydroxymethyl)ethoxy)methyl)-HCID 178418582HCID 178418582, compound

Product 1

HCID 3006458HCID 3006458, compound

Conditions

Temperature
0 °C

Procedure

Dry H2S was passed through a NaOCH3 solution (1 M) (6 mL) with magnetic stirring and cooling at 0° C. for 10 minutes. Compound 18a (0.13 g; 0.5 mmole) was then added in one portion to the stirred solution of NaSH which had been generated in situ as described above. The mixture was stirred at room temperature for 4 hours and then allowed to stand at 0° C. for an additional 12 hours. The mixture was filtered and the filtrate conc. in vacuo. The residue was purified by a column (2×40 cm; prepacked in CH2Cl2) of silica gel (20 g; 70-230 mesh). Elution of the column with CH2Cl2 :CH3OH (94:6) gave the title compound, which was crystallized from H2O to afford pure 18c (0.04 g; yield 28%); m.p. 180°-181° C.; IR (KBr) γ3400 and 3180 (NH2, OH), 1640 cm-1 ; UVλmax nm: (pH 1), 241 (2750) 301 (1220); MeOH, 283 (5387); pH 11, 216 (26200) 278 (5806); 1H NMR (DMSO-d6): δ3.3-3.45 (m, 4H, H-3', H-4'), 3.60 (m, 1H, H-4'), 4.62 (t, 2H, OH), 5.65 (s, 2H, H-1'), 7.9 (s, 1H, C6 --H), 7.98 (brs, 2H, D2O exchangeable, NH2), 8.15 (s, 1H, C2 --H), 9.45 and 9.60 (brs, 1 each, D2O exchangeable, CSNH2). Anal. (C11H15N5O3S.H2O). (C,H,N).

Workup

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. filtrationThe mixture was filtered
  3. customThe residue was purified by a column (2×40 cm; prepacked in CH2Cl2) of silica gel (20 g; 70-230 mesh)
  4. washElution of the column with CH2Cl2 :CH3OH (94:6)

Sources & evidence

ORD record
ord-8d48a86b0d7843a0a1c641bdcccd2b7f
Source dataset
uspto-grants-1990_11
Patent number
US04968686

Reaction notes

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