Methylamine → Regadenoson

HRID 2168566Notes

Reaction equation

HRID 2168566 reaction equation
[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([N:20]1[CH:24]=[C:23]([C:25]([O:27]CC)=O)[CH:22]=[N:21]1)=[N:14][C:15]=2[NH2:19].[CH3:30][NH2:31]>>[OH:1][C@@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:8][OH:9])[O:4][C@H:3]1[N:10]1[CH:18]=[N:17][C:16]2[C:11]1=[N:12][C:13]([N:20]1[CH:24]=[C:23]([C:25]([NH:31][CH3:30])=[O:27])[CH:22]=[N:21]1)=[N:14][C:15]=2[NH2:19]

Participants

3

Reactant 2

HCID 6329MethylamineHCID 9865974Ethyl 1-(6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-2-yl)-1H-pyrazole-4-carboxylate

Product 1

HCID 219024Regadenoson

Conditions

Temperature
65 °C

Procedure

Compound 12 (0.05 mg, 0.12 mmol) was added to 4 mL methylamine (40% sol. in water). The mixture was heated at 65° C. for 24 h. After concentration in vacuo, the residue was purified using prep. TLC (10% MeOH:DCM). 1HNMR(CD3OD) δ2.90 (s, 3 H), 3.78 (m, 1 H), 3.91 (m, 1 H), 4.13 (d, 1 H), 4.34 (d, 1 H), 4.64 (m, 1 H), 6.06 (d, 1 H), 8.11 (s, 1 H), 8.38 (s, 1 H), 9.05 (s, 1 H).

Workup

  1. concentrationAfter concentration in vacuo
  2. customthe residue was purified

Sources & evidence

ORD record
ord-e06a27c42c924c75979ce2851ba49bf8
Source dataset
uspto-grants-2015_06
Patent number
US09045519B2

Reaction notes

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