Potassium Carbonate → 5-Amino-7-cyclopropylmethoxy-3-beta-D-ribofuranosyl-thiazolo [4,5-d]pyrimidin-2-one

HRID 19479Notes

Reaction equation

HRID 19479 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([O:30][CH2:31][CH:32]2[CH2:34][CH2:33]2)[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][O:26]C(=O)C)[C@@H:18]([O:19]C(=O)C)[C@H:13]3[O:14]C(=O)C)[C:6]=2[N:7]=1.C([O-])([O-])=O.[K+].[K+]>CO>[NH2:1][C:2]1[N:3]=[C:4]([O:30][CH2:31][CH:32]2[CH2:34][CH2:33]2)[C:5]2[S:10][C:9](=[O:11])[N:8]([C@@H:12]3[O:24][C@H:23]([CH2:25][OH:26])[C@@H:18]([OH:19])[C@H:13]3[OH:14])[C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 685595075-Amino-7-cyclopropylmethoxy-3-(2',3',5'-tri-O-acetyl-beta-D-ribofuranosyl)-thiazolo[4,5-d]pyrimidin-2-one

Product 1

HCID 596448095-Amino-7-cyclopropylmethoxy-3-beta-D-ribofuranosyl-thiazolo [4,5-d]pyrimidin-2-oneYield 29.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 62 (570 mg, 1.18 mmol) in MeOH was added K2CO3 (50 mg, 0.36 mmol) at room temperature. The reaction mixture was stirred 1 h, concentrated, partitioned between 20% IPA-CHCl3 and water, and then triturated with Et2O to afford 128 mg (29%) of 63 as a white solid: 1H (400 MHz, d6-DMSO) δ 6.86 (s, 2H), 5.85 (d, J=5.1 Hz, 1H), 5.27 (d, J=5.5 Hz, 1H), 4.96 (d, J=5.5 Hz, 1H), 4.77 (q, J=5.5 Hz, 1H), 4.66 (t, J=5.9 Hz, 1H), 4.18 (dd, J=7.3, 1.1 Hz, 1H), 4.09 (q, J=5.5 Hz, 1H), 3.75 (q, J=5.1 Hz, 1H), 3.39-3.60 (m, 2H), 1.20-1.27 (m, 1H), 0.53-0.57 (m, 2H), 0.31-0.34 (m, 2H); MS (+)-ES [M+H]+ m/z 371. Elemental Analysis calc'd for C14H18N4O6S: C, 45.40; H, 4.90; N, 15.13; S, 8.66. Found: C, 44.98; H, 4.92; N, 14.92; S, 8.49.

Workup

  1. concentrationconcentrated
  2. custompartitioned between 20% IPA-CHCl3 and water
  3. customtriturated with Et2O

Sources & evidence

ORD record
ord-99ec2bc3345b493ba10e9c580586c49b
Source dataset
uspto-grants-2010_06
Patent number
US07745415B2

Reaction notes

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