Hydrochloric Acid → HCID 57083073, compound

HRID 1684707Notes

Reaction equation

HRID 1684707 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=[S:19])[C:5]2[N:6]=[CH:7][N:8]([C@H:11]3[CH2:15][C@H:14]([OH:16])[C@@H:13]([CH2:17][OH:18])[CH2:12]3)[C:9]=2[N:10]=1.[OH-].[Na+].[CH2:22](Cl)[CH:23]=[CH2:24].Cl>>[CH2:24]([S:19][C:4]1[N:3]=[C:2]([NH2:1])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[C@H:11]1[CH2:15][C@H:14]([OH:16])[C@@H:13]([CH2:17][OH:18])[CH2:12]1)[CH:23]=[CH2:22]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 7850Allyl chlorideHCID 14798Sodium HydroxideHCID 178508221HCID 178508221, compound

Product 1

HCID 57083073HCID 57083073, compound

Procedure

(+)-(1S, 2R, 4R)-4-(2-Amino-1,6-dihydro-6-thioxo-9H-purin-9-yl)-2-(hydroxymethyl)-1-cyclopentanol (351 mg, 1.25 mmol) and 1N sodium hydroxide (1.25 mL) were stirred with allyl chloride (0.15 mL) for 5 hours. The solution was neutralized with hydrochloric acid and volatiles evaporated. The residue was chromatographed on silica gel. Title compound was eluted with 12% methanol-chloroform as a white solid foam which solidified to white powder from acetonitrile (240 mg, 60%); m.p. 133-134°; mass spectrum (Cl, CH4):322 (M+1);1H-NMR (DMSO d6)δ: 8.07 (s, 1, H8), 6.51 (br s, 2, NH2), 6.10-5.85 (m, 1, CH=), 5.45-5.30 (m, 1, 1/2CH2 =),5.15-5.05 (m, 1, 1/2CH2 =), 5.0-4.8 (m, 1, CHN), 4.79 (d, J=4.1 Hz, 1, OH), 4.66 (t, J=5.2 Hz, 1, CH2OH), 4.15-4.0 (m, 1, CHO), 3.98 (d, J=6.9 Hz, 2, CH2S), 3.6-3.4(m, 2, CH2O), 2.4-1.9(m, 4, CH +methylenes), 1.7-1.55 (m, 1, 1/2CH2); [α]20589 +9.30°, [α]20578 +9.68°, [α]20546 +11.1°, [α]20436 +18.6°, [α]20365 +25.4°(c=0.79, methanol).

Workup

  1. customevaporated
  2. customThe residue was chromatographed on silica gel
  3. washTitle compound was eluted with 12% methanol-chloroform as a white solid foam which

Sources & evidence

ORD record
ord-eccabd868a8f48e59f0a4525e18a84ff
Source dataset
uspto-grants-1997_06
Patent number
US05641889

Reaction notes

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