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

HRID 1850677Notes

Reaction equation

HRID 1850677 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

To a solution of phenylsilane (478.5 mg, 550.0 μL, 4.422 mmol) and allyl 2-amino-5-[2-(dimethylamino)ethoxy]pyrazolo[1,5-a]pyrimidine-3-carboxylate (900 mg, 2.948 mmol) in DCM (5 mL) was added palladium triphenylphosphane (170.3 mg, 0.1474 mmol). The reaction mixture was stirred at room temperature for 3 h. Ether was slowly added to the mixture and a white solid precipitated. This solid was filtered off, washed with small amount of diethyl ether and dried to afford pure 2-amino-5-(2-(dimethylamino)ethoxy)pyrazolo[1,5-a]pyrimidine-3-carboxylic acid as off-white solid. (530 mg, 67% yield).

Workup

  1. customa white solid precipitated
  2. filtrationThis solid was filtered off
  3. washwashed with small amount of diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-8593435682df4cd6bd32b8c9db9f2a43
Source dataset
uspto-grants-2015_02
Patent number
US08957078B2

Reaction notes

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