Triphenylphosphine → 3-[7-(2-chlorobenzyl)-5-methyl-2-(1-naphthylmethyl)-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl]benzoic acid

HRID 1181799Notes

Reaction equation

HRID 1181799 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[C:9]([C:23]3[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=3)[C:26]([OH:28])=[O:27])[N:10]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[N:11]=[C:5]2[NH:4][C:3]1=[O:32].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[CH2:59]O>C1COCC1>[Cl:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][C:54]=1[CH2:59][N:4]1[C:5]2=[N:11][N:10]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[C:9]([C:23]3[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=3)[C:26]([OH:28])=[O:27])=[C:6]2[C:7](=[O:8])[N:2]([CH3:1])[C:3]1=[O:32]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 288102-Chlorobenzyl alcoholHCID 1363341153-[5-methyl-2-(1-naphthylmethyl)-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl]benzoic acid

Product 1

HCID 589810073-[7-(2-chlorobenzyl)-5-methyl-2-(1-naphthylmethyl)-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl]benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisipropylazodicarboxylate (0.157 g) was added to a mixture of resin bound 3-[5-methyl-2-(1-naphthylmethyl)-4,6-dioxo-4,5,6,7-tetrahydro-2H-pyrazolo[3,4-d]pyrimidin-3-yl]benzoic acid (0.120 g), triphenylphosphine (0.204 g), and 2-chlorophenylmethanol in dry THF (2 mL) at −15° C. Reaction temperature was allowed to come to room temperature and shaken for 20 h. The resin was filtered, washed (3 times) DMF, CH2Cl2, MeOH, CH2Cl2, and dried in vacuum. The dry resin was treated with 15% TFA in dichloromethane (1 mL) for 2 h, and filtered and washed (2 times) with dichloromethane. Combined filtrates were concentrated, and dried in vacuum to give the title compound (0.062 g). Mass 548.80 (M+H).

Workup

  1. additionDiisipropylazodicarboxylate (0.157 g) was added to a mixture of resin
  2. customat −15° C
  3. customReaction temperature
  4. customto come to room temperature
  5. filtrationThe resin was filtered
  6. washwashed (3 times) DMF, CH2Cl2, MeOH, CH2Cl2
  7. customdried in vacuum
  8. additionThe dry resin was treated with 15% TFA in dichloromethane (1 mL) for 2 h
  9. filtrationfiltered
  10. washwashed (2 times) with dichloromethane
  11. concentrationCombined filtrates were concentrated
  12. customdried in vacuum

Sources & evidence

ORD record
ord-e86912f4afb6423c8f0b61b82905bea7
Source dataset
uspto-grants-2007_10
Patent number
US07285558B2

Reaction notes

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