Ethanol → 2-Hydroxymethyl-4-methyl-8-[2'-(1-tert-butyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

HRID 129011Notes

Reaction equation

HRID 129011 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:14]3[N:15]=[C:16]([CH2:19][OH:20])[N:17]=[CH:18][C:13]=3[CH2:12][CH:11](C)[C:10]2=[O:22])=[CH:4][CH:3]=1.[C:23]([N:27]1[C:31]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2B(O)O)=[N:30][N:29]=[N:28]1)([CH3:26])([CH3:25])[CH3:24].[C:41]([O-])([O-])=O.[Na+].[Na+].CCO>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[OH:20][CH2:19][C:16]1[N:17]=[C:18]([CH3:41])[C:13]2[CH2:12][CH2:11][C:10](=[O:22])[N:9]([CH2:8][C:5]3[CH:4]=[CH:3][C:2]([C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][C:32]=4[C:31]4[N:27]([C:23]([CH3:26])([CH3:25])[CH3:24])[N:28]=[N:29][N:30]=4)=[CH:7][CH:6]=3)[C:14]=2[N:15]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 109447112-[(1-tert-Butyl)-1H-tetrazol-5-yl]phenylboronic acidHCID 193729978-[(4-bromophenyl)methyl]-2-hydroxymethyl-6-methyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one

Product 1

HCID 193729942-Hydroxymethyl-4-methyl-8-[2'-(1-tert-butyl-1H-tetrazol-5-yl)biphenyl-4-ylmethyl]-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-oneYield 90%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 8-[(4-bromophenyl)methyl]-2-hydroxymethyl-6-methyl-5,8-dihydro-6H-pyrido[2,3-d]pyrimidin-7-one (0.95 g, 2.62 mmol), 2-[(1-tert-butyl)-1H-tetrazol-5-yl]phenylboronic acid (0.72 g, 2.90 mmol) (prepared according to J. W. Ellingboe, et al. U.S. Pat. No. 5,149,699), 2M Na2CO3 (5.5 mL), tetrakis(triphenylphosphine)palladium(0) (100 tug, 0.086 mmol), EtOH (3 mL)and toluene (16 mL) was heated under reflux for 20 h. The mixture was diluted with CH2Cl2 and the layers were separated. The organic phase was dried (MgSO4) and concentrated to give an orange oil. Purification by flash chromatography (4% MeOH/CH2Cl2) gave 1.20 g (90%) of product as a colorless foam.

Workup

  1. customprepared
  2. temperatureunder reflux for 20 h
  3. customthe layers were separated
  4. dry with materialThe organic phase was dried (MgSO4)
  5. concentrationconcentrated
  6. customto give an orange oil
  7. customPurification by flash chromatography (4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-218727b6fe7e4875878e95f9a3b1ecb4
Source dataset
uspto-grants-1995_11
Patent number
US05466692

Reaction notes

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