HCID 178497681, compound → 4-[2-(2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pyrido[2,3-d]pyrimidin-6-yl)ethyl]-1H-pyrrole-2-carboxylic acid

HRID 1108269Notes

Reaction equation

HRID 1108269 reaction equation
C([NH:7][C:8]1[N:9]=[C:10]([OH:39])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([C:35]([O:37]C)=[O:36])[N:23]([Si](C(C)C)(C(C)C)C(C)C)[CH:24]=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:39])[C:11]2[CH2:17][CH:16]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([C:35]([OH:37])=[O:36])[NH:23][CH:24]=3)[CH2:15][NH:14][C:12]=2[N:13]=1

Participants

3

Reactant 1

HCID 178497681HCID 178497681, compound

Product 1

HCID 1785088944-[2-(2-amino-4-oxo-5,6,7,8-tetrahydro-1H-pyrido[2,3-d]pyrimidin-6-yl)ethyl]-1H-pyrrole-2-carboxylic acidYield 94%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A suspension of methyl 4-[2-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]-1-triisopropylsilylpyrrole-2-carboxylate (390.4 mg, 0.7 mmol) in 1N sodium hydroxide (1 mL) was heated under reflux until clear (about 4 hours). The mixture was cooled to room temperature, extracted with ethyl acetate, and then acidified with glacial acetic acid. The solid which formed was collected by filtration, washed with water, and dried in vacuo to give 4-[2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]pyrrole-2-carboxylic acid (199 mg, 94%), mp >260° C.: 1H NMR (DMSO-d6) δ 11.39 (s, 1H), 9.72 (br s, 1H), 6.73 (s, 1H), 6.55 (s, 1H), 6.25 (s, 1H), 5.93 (s, 2H), 3.16 (br d, 1H, J=9.5 Hz), 2.72 (m, 1H), 2.43 (m, 3H), 1.75 (m, 1H), 1.42-1.53 (m, 3H); 1H NMR (CD3OD) δ 6.69 (s, 1H), 6.63 (s, 1H), 3.31 (brd, 1H, J=12.1 Hz), 2.91 (dd, 1H, J=12.1, 9.2 Hz), 2.67 (dd, 1H, J=15.3, 4.4 Hz), 2.55 (m, 2H), 1.99 (dd, 1H, J=15.3, 9.4 Hz), 1.76 (m, 1H), 1.60 (m, 2H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux until clear (about 4 hours)
  3. extractionextracted with ethyl acetate
  4. customThe solid which formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-520ac2d330154e2d8a7159bf5a89c81e
Source dataset
uspto-grants-2000_05
Patent number
US06066639

Reaction notes

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