Sodium Hydroxide → HCID 178508891, compound

HRID 1108271Notes

Reaction equation

C([NH:7][C:8]1[N:9]=[C:10]([OH:30])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[NH:24][N:23]=[C:22]([C:25]([O:27]CC)=[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:30])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[NH:24][N: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 178468819HCID 178468819, compound

Product 1

HCID 178508891HCID 178508891, compoundYield 80.6%

Procedure

Upon saponification of ethyl 5-[2-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]pyrazole-3-carboxylate (637 mg, 1.5 mmol) with 1N sodium hydroxide (3 mL) as described in Example 11, there is obtained 5-[2-(amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]pyrazole-3-carboxylic acid (368 mg, 80%, mp >260° C.): 1H NMR (DMSOd6) δ 12.90 (br s, 1H), 9.85 (br s, 1H), 6.67 (s, 1H), 6.42 (s, 1H), 6.27 (s, 1H), 5.96 (s, 2H), 3.16 (br d, 1H, J=107 Hz), 2.74 (m, 1H), 2.65 (m, 1H), 2.46 (brd, 1H, J=15.0 Hz), 1.90 (dd, 1H, J=15.0, 7.9 Hz), 1.68-1.47 (m, 3H).

Sources & evidence

ORD record: ord-136f33ad5d1f45e4a8ed60db09b19c12
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06066639

Reaction notes

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