Sodium Hydroxide → HCID 19791979, compound

HRID 1655578Notes

Reaction equation

HRID 1655578 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[N:26]([C:27]([C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:25]=[N:24][N:23]=3)=[CH:12][CH:11]=2)[C:5]([C:46]([O:48]CC)=[O:47])=[CH:4][N:3]=1.[OH-].[Na+]>>[CH3:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]3[N:26]([C:27]([C:40]4[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=4)([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[N:25]=[N:24][N:23]=3)=[CH:14][CH:15]=2)[C:5]([C:46]([OH:48])=[O:47])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 19791754HCID 19791754, compound

Product 1

HCID 19791979HCID 19791979, compound

Procedure

Ethyl 2-methyl-4-{N-[(2'-[N-triphenylmethyl-tetrazol-5-yl]biphenyl-4-yl)methyl]amino}pyrimidine-5-carboxylate was hydrolyzed with sodium hydroxide and neutralized with one equivalent of hyochloric acid to give 2-methyl-4-{N-[(2'-[N-triphenylmethyl-tetrazol-5-yl]biphenyl-4-yl)methyl]amino}pyrimidine-5-carboxylic acid. This compound was treated with thionyl chloride at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and the residue obtained dissolved in methylene chloride and cooled to 0° C. Ammonia was added, and the reaction mixture was stirred at 0° C. for several hours. The solvent was removed under reduced pressure and the residue obtained chromatographed on silica gel. The triphenylmethyl protecting group was removed with aqueous hydrochloric acid in dioxane to give the title compound in high yield. 1H NMR (DMSO-d6, 300 MHz) d 0.85 (t, J=7 Hz, 3H), 1.22 (m, 2H), 1.55 (m, 2H), 2.55 (s, 3H), 3.58 (m, 2 H), 5.00 (s, 2H), 7.08 (d, J=7 Hz, 2H), 7.25 (d, J=7 Hz, 2H), 7.55 (d, J=7 Hz, 1H), 7.59 (d, J=7 Hz, 1H), 7.68 (m, 2H), 8.01 (s, 1H), 8.40 (s, 1H), 8.42 (s, 1H). MS (DCl/NH3) m/e 443 (M+H)+.

Sources & evidence

ORD record
ord-eb20a803992c4500b7d5ae4c3f420db8
Source dataset
uspto-grants-1993_10
Patent number
US05250548

Reaction notes

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