Diethyl Ether → 2-Amino-5-(2-(dimethylamino)ethoxy)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 869117Notes

Reaction equation

HRID 869117 reaction equation
C1([SiH3])C=CC=CC=1.[NH2:8][C:9]1[C:23]([C:24]([O:26]CC=C)=[O:25])=[C:12]2[N:13]=[C:14]([O:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[CH:15]=[CH:16][N:11]2[N:10]=1.CCOCC>C(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[NH2:8][C:9]1[C:23]([C:24]([OH:26])=[O:25])=[C:12]2[N:13]=[C:14]([O:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[CH:15]=[CH:16][N:11]2[N:10]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 12752PhenylsilaneHCID 90412007Allyl 2-amino-5-(2-(dimethylamino)ethoxy)pyrazolo[1,5-a]pyrimidine-3-carboxylate

Product 1

HCID 904115212-Amino-5-(2-(dimethylamino)ethoxy)pyrazolo[1,5-a]pyrimidine-3-carboxylic acidYield 67%

Reagents, catalysts & solvents 2

HCID 15220664Palladium--triphenylphosphane (1/1)CatalystHCID 6344DichloromethaneSolvent

Procedure

Palladium triphenylphosphane (170.3 mg, 0.1474 mmol) was added to a solution of phenylsilane (478.5 mg, 550 μL, 4.422 mmol) and allyl 2-amino-5-[2-(dimethylamino)ethoxy]pyrazolo[1,5-a]pyrimidine-3-carboxylate 4b (900 mg, 2.948 mmol) in DCM (5 mL). The reaction mixture was stirred at room temperature for 3 h. Ether was slowly added and the white solid was then filtered off, washed with small amount of diethyl ether and dried to afford pure product as off-white solid (yield 67%); LC-MS (M+H)+=266.1; 1H NMR (500 MHz, DMSO-d6) δ 12.35 (brs, 1H), 9.65 (brs, 1H), 8.72 (d, 1H), 6.55 (d, 1H), 6.25-6.15 (m, 2H), 4.73-4.70 (m, 2H), 3.58-3.55 (m, 2H), 2.90 (s, 6H);

Workup

  1. filtrationthe white solid was then filtered off
  2. washwashed with small amount of diethyl ether
  3. customdried

Sources & evidence

ORD record
ord-88633c0cc2064cf49fbeae876188b492
Source dataset
uspto-grants-2015_03
Patent number
US08969360B2

Reaction notes

Loading…