Sodium Bicarbonate → HCID 178508221, compound

HRID 581224Notes

Reaction equation

HRID 581224 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:15][C@H:14]([OH:16])[C@@H:13]([CH2:17][OH:18])[CH2:12]2)=[C:4](Cl)[N:3]=1.NC(N)=[S:22].C(=O)(O)[O-].[Na+]>O>[NH2:1][C:2]1[NH:3][C:4](=[S:22])[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

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723790ThioureaHCID 11108834HCID 11108834, compound

Product 1

HCID 178508221HCID 178508221, compoundYield 71.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(+)-(1S,2R,4R)-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-(hydroxymethyl)cyclopentanol, (1.70 g, 6.00 mmol) and thiourea (456 mg, 6.00 mmol) were refluxed in water (15 mL) for 1.0 hour. The cooled solution was adjusted to pH5 with saturated aqueous sodium bicarbonate. The resulting precipitate was filtered, washed with water and dried to give title compound as white powder (1.20 g, 71%); m.p. 290-291° dec; mass spectrum (Cl, CH4) 282 (M+1); 1H-NMR (DMSO-d6)δ: 11.90 (br s, 1, NH), 8.03 (s, 1, H-8), 6.78 (br s, 2, NH2), 4.95-4.70 (m, overlapping d at 4.78, J=27 Hz, total 2, CHN and OH), 4.7-4.6 (m, 1, CH2OH), 4.1-4.0 (m, 1, CHOH), 3.6-3.4 (m, 2, CH2O), 2.4-2.2 (m, 1, CH), 2.2-1.9 (m, 3, methylene), 1.7-1.5 (m, 1, 1/2CH2); [α]20589 +6.43°, [α]20578 +6.71°, [α]20546 +7.43°, [α]20436 +8.43°, [α]20 365 +8.43° (c=0.70, 0.1N NaOH).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-401c06c0836e4a3083a41966c11eadb1
Source dataset
uspto-grants-1999_07
Patent number
US05919941

Reaction notes

Loading…