Hydroxyamine hydrochloride → HCID 178508888, compound

HRID 1957561Notes

Reaction equation

HRID 1957561 reaction equation
[Na].Cl.[NH2:3][OH:4].C([NH:11][C:12]1[N:13]=[C:14]([OH:33])[C:15]2[CH2:21][CH:20]([CH2:22][CH2:23][C:24]3[S:28][C:27]([C:29](OC)=[O:30])=[CH:26][CH:25]=3)[CH2:19][NH:18][C:16]=2[N:17]=1)(=O)C(C)(C)C>CO>[NH2:11][C:12]1[N:13]=[C:14]([OH:33])[C:15]2[CH2:21][CH:20]([CH2:22][CH2:23][C:24]3[S:28][C:27]([C:29]([NH:3][OH:4])=[O:30])=[CH:26][CH:25]=3)[CH2:19][NH:18][C:16]=2[N:17]=1

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochloride2×HCID 5360545SodiumHCID 178497707HCID 178497707, compound

Product 1

HCID 178508888HCID 178508888, compoundYield 77.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 10 mL of anhydrous methanol was added 0.33 g (14.4 mmol) of sodium metal and a solution of 0.050 g (0.72 mmol) of hydroxylamine hydrochloride in 7 mL of methanol was then added. The resulting reaction mixture was stirred for 15 minutes and 0.23 g (0.5 mmol) of methyl 5-[2-(2-pivaloylamino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]thien-2-ylcarboxylate was added under nitrogen. The reaction mixture was stirred for 30 minutes, 0.011 g (0.16 mmol) of hydroxylamine hydrochloride was added, and the reaction was stirred a total of 4.5 hours, and then filtered. The filtrate was then treated with diethyl ether and the solid collected and dried in vacuo to give 0.13 g (71%) of N-{5-[2-(2-amino-4-hydroxy-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidin-6-yl)ethyl]thien-2-ylcarbonyl}hydroxylamine as a tan colored solid. Rf=0.09 (10% CH3OH/CHCl3); 1H NMR (300 MHz, DMSOd6 /TFAd4) δ1.55-1.70 (m, 4H), 1.83; 1.91 (m, 1H), 2.82-2.87 (m, 4H), 3.29-3.33 (m, 1H), 6.82 (d, J=3.6 Hz, 1H), 7.43 (d, J=1.4 Hz, 1H);

Workup

  1. customThe resulting reaction mixture
  2. stirringThe reaction mixture was stirred for 30 minutes
  3. stirringthe reaction was stirred a total of 4.5 hours
  4. filtrationfiltered
  5. additionThe filtrate was then treated with diethyl ether
  6. customthe solid collected
  7. customdried in vacuo

Sources & evidence

ORD record
ord-87d70c8917eb49baa984eb8a2c8dc42b
Source dataset
uspto-grants-1998_07
Patent number
US05786358

Reaction notes

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