Bicarbonate Ion → 4-(t-Butyldimethylsiloxyphenyl)pyrimidine

HRID 2259529Notes

Reaction equation

HRID 2259529 reaction equation
C(OC1C=N[C:12]([C:15]2[CH:20]=[CH:19][C:18](O)=[CH:17][CH:16]=2)=[N:13][CH:14]=1)C1C=CC=CC=1.N1[CH:26]=[CH:25][N:24]=C1.[Si:27](Cl)([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28].C(=O)(O)[O-:36]>CN(C)C=O>[O:36]([C:20]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:12]1[CH:26]=[CH:25][N:24]=[CH:14][N:13]=1)[Si:27]([C:30]([CH3:33])([CH3:32])[CH3:31])([CH3:29])[CH3:28]

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 1357441904-[5-(Benzyloxy)pyrimidin-2(1H)-ylidene]cyclohexa-2,5-dien-1-one

Product 1

HCID 1317192164-(t-Butyldimethylsiloxyphenyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-benzyloxy-2-(4-hydroxyphenyl)pyrimidine (Sg, 0.0180 moles) (prepared essentially as in Example 1) and imidazole (2.5g, 0.0360 moles) in N,N-dimethylformamide (DMF) (50 ml) was added 2.7 g (0.0180 moles) of t-butyldimethylsilylchloride. The resulting mixture was stirred at room temperature for 4 weeks. The stirred mixture was then poured into 100 ml of dilute bicarbonate, and the resulting solid was collected by filtration. After recrystallization from methanol, the solid was hydrogenated at 60 psi (3100 torr) with catalytic 10% palladium on carbon for 48 hours. The catalyst was then removed by filtration, and the solvent was removed on a rotary evaporator to yield 2.4 g of 5-hydroxy-2-(4-(t-butyldimethylsiloxyphenyl)pyrimidine.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. customAfter recrystallization from methanol
  3. customThe catalyst was then removed by filtration
  4. customthe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-d5a021a0e03e49ad9a137860199d0e8f
Source dataset
uspto-grants-1995_12
Patent number
US05474705

Reaction notes

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