Methanesulfonic Acid → 4-Hydroxymethyl-2-meth yl-8-[2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

HRID 129015Notes

Reaction equation

HRID 129015 reaction equation
[OH:1][CH2:2][C:3]1[C:4]2[CH2:13][CH2:12][C:11](=[O:14])[N:10]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]4[N:32](C(C)(C)C)[N:31]=[N:30][N:29]=4)=[CH:18][CH:17]=3)[C:5]=2[N:6]=[C:7]([CH3:9])[N:8]=1.CS(O)(=O)=O>C1(C)C=CC=CC=1>[OH:1][CH2:2][C:3]1[C:4]2[CH2:13][CH2:12][C:11](=[O:14])[N:10]([CH2:15][C:16]3[CH:17]=[CH:18][C:19]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[C:28]4[NH:32][N:31]=[N:30][N:29]=4)=[CH:20][CH:21]=3)[C:5]=2[N:6]=[C:7]([CH3:9])[N:8]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 193730024-hydroxymethyl-2-methyl-8-[2'-(1-tert-butyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 1784329704-Hydroxymethyl-2-meth yl-8-[2'-(1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-oneYield 19.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-hydroxymethyl-2-methyl-8-[2'-(1-tert-butyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one (550 mg, 1.14 mmol), methanesulfonic acid (1.10 g, 11.40 mmol), and toluene (10 mL) was heated under reflux for 4 days. The mixture was concentrated, 1N KOH (11.4 mL) was added, and the mixture was extracted with CHCl3 (discarded). The aqueous phase was acidified to pH4-5 with 1N HCl and extracted with CHCl3. The extracts were dried and concentrated to give 94 mg of a yellow foam. Trituration with acetone and recrystallization from EtOH gave 46 mg (9%) of product as a white solid, mp 246°-247° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 days
  3. concentrationThe mixture was concentrated
  4. addition1N KOH (11.4 mL) was added
  5. extractionthe mixture was extracted with CHCl3 (discarded)
  6. extractionextracted with CHCl3
  7. customThe extracts were dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-85207125f9f84de9a5ff1d4f7615041e
Source dataset
uspto-grants-1995_11
Patent number
US05466692

Reaction notes

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