Sodium Hydroxide → HCID 178508890, compound

HRID 1108270Notes

Reaction equation

C([NH:7][C:8]1[N:9]=[C:10]([OH:29])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[NH:24][CH:23]=[C:22]([C:25]([O:27]C)=[O:26])[CH:21]=3)[CH2:15][NH:14][C:12]=2[N:13]=1)(=O)C(C)(C)C.[OH-].[Na+]>>[NH2:7][C:8]1[N:9]=[C:10]([OH:29])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[NH:24][CH:23]=[C:22]([C:25]([OH:27])=[O:26])[CH:21]=3)[CH2:15][NH:14][C:12]=2[N:13]=1

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 178498879HCID 178498879, compound

Product 1

HCID 178508890HCID 178508890, compound

Procedure

Upon saponification of methyl 5-[2-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]pyrrole-3-carboxylate (401 mg g, 1.0 mmol) with 1N sodium hydroxide (15 mL) as described in Example 11, there is obtained 5-[2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]pyrrole-3-carboxylic acid, mp >260° C.: 1H NMR (DMSO-d6) δ 11.49 (s, 1H), 10.12 (br s, 1H), 9.66 (s, 1H), 7.16 (s, 1H), 6.23 (s, 1H), 6.05 (s, 2H), 5.90 (s, 1H), 3.16 (brd, 1H, J=10.9 Hz), 2.78 (m, 1H), 2.63-2.40 (m, 2H), 1.77 (dd, 1H, J=15.2, 8.6 Hz), 1.69-1.43 (m, 3H).

Sources & evidence

ORD record: ord-6826985df58a49908f38c43d715d78fa
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06066639

Reaction notes

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