Ammonia → 1-[6-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid amide

HRID 350599Notes

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]([NH:27]C)=[O:26])[CH:22]=[N:21]1)=[N:14][C:15]=2[NH2:19].N>>[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]([NH2:27])=[O:26])[CH:22]=[N:21]1)=[N:14][C:15]=2[NH2:19]

Participants

Reactant 2

HCID 222Ammonia

HCID 219024Regadenoson

Product 1

HCID 98644451-[6-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-9H-purin-2-yl]-1H-pyrazole-4-carboxylic acid amide

Procedure

Compound 20 was prepared in a manner similar to that of compound 16 using ammonia instead of methylamine, MS 377.25 (M+1).

Sources & evidence

ORD record: ord-db5090e43c6d4590a823d3e339062ada
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183264B2

Reaction notes

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