1-Aminopyrrole → 2-Phenylpyrimidine-5-carboxylic acid

HRID 2381978Notes

Reaction equation

HRID 2381978 reaction equation
N1(N)C=CC=C1.C[O:8]C(=O)CCC1C(=O)N(N)C(=O)NC=1.N1(N[C:28]([C:30]2[CH:31]=[N:32][C:33]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[N:34][CH:35]=2)=[O:29])C=CC=C1>>[C:36]1([C:33]2[N:32]=[CH:31][C:30]([C:28]([OH:29])=[O:8])=[CH:35][N:34]=2)[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

4

Reactant 3

HCID 1365891-AminopyrroleHCID 250997822-Phenyl-pyrimidine-5-carboxylic acid pyrrol-1-ylamideHCID 866393703-Amino-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-propionic acid methyl ester

Product 1

HCID 7473892-Phenylpyrimidine-5-carboxylic acid

Procedure

Following procedures similar to those of Example 64 but substituting pyrrol-1-ylamine for 3-{3-amino-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-propionic acid methyl ester, there is prepared 2-phenyl-pyrimidine-5-carboxylic acid pyrrol-1-ylamide (62%) as a solid. MS: 265 (M+H); 1H NMR (300 MHz, CDCl3): δ 6.25 (d, 2H), 6.76 (d, 2H), 7.48-7.63 (m, 3H), 8.52 (d, 2H), 8.95-9.60 (br, 2H).

Sources & evidence

ORD record
ord-88178fc25e3c45fcafa570f7f9acde46
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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