Phthalic Anhydride → HCID 136348493, compound

HRID 510401Notes

Reaction equation

HRID 510401 reaction equation
[NH2:1][C:2]1[C:12]([CH2:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)=[C:5]2[NH:6][C:7](=[O:11])[CH2:8][C:9](=[O:10])[N:4]2[N:3]=1.[C:24]1(=O)[O:29][C:27](=[O:28])[C:26]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:25]12>C(#N)C>[O:28]=[C:27]1[C:26]2[C:25](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:24](=[O:29])[N:1]1[C:2]1[C:12]([CH2:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=[CH:16][CH:15]=2)=[C:5]2[NH:6][C:7](=[O:11])[CH2:8][C:9](=[O:10])[N:4]2[N:3]=1

Participants

4

Reactant 2

HCID 6811Phthalic Anhydride2×HCID 136348492HCID 136348492, compound

Product 1

HCID 136348493HCID 136348493, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

The solution of 2-amino-3-(1-naphthalenylmethyl)pyrazolo[1,5-a]pyrimidine-5,7(4H,6H)-dione (2.7 g, 8.81 mmol), phthalic anhydride (3.00 g, 20.27 mmol) in Acetonitrile (100 mL) was stirred at 80° C. for 2 days. Additional phthalic anhydride (3.00 g, 20.27 mmol) was added in. The reaction was stirred at 80° C. for 5 days. The reaction was concentrated. To the crude was added DCM (20 mL). The insoluble solid was collected. The filtrate was purified on a silica column (20-60% EtOAc/Hexane) which was combined with the solid from filtration to give the product (2.8 g, 71%). LC/MS: MS (ES+) m/e 437.2 [M+H]+

Workup

  1. concentrationThe reaction was concentrated
  2. additionTo the crude was added DCM (20 mL)
  3. customThe insoluble solid was collected
  4. customThe filtrate was purified on a silica column (20-60% EtOAc/Hexane) which
  5. filtrationwas combined with the solid from filtration

Sources & evidence

ORD record
ord-46592ca6414f4638a287f453312892a2
Source dataset
uspto-grants-2015_08
Patent number
US09096605B2

Reaction notes

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