Hydrochloric Acid → HCID 18617749, compound

HRID 1264304Notes

Reaction equation

HRID 1264304 reaction equation
C[O:2][CH:3](OC)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][C:13]([O:16][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)=[N:14][CH:15]=2)=[CH:6][CH:5]=1.Cl>C1COCC1>[O:16]=[C:13]1[N:12]=[CH:11][C:10]([C:7]2[CH:8]=[CH:9][C:4]([CH:3]=[O:2])=[CH:5][CH:6]=2)=[CH:15][NH:14]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57142883HCID 57142883, compound

Product 1

HCID 18617749HCID 18617749, compoundYield 116.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-[t-butyldiphenylsilyloxy]-pyrimidin-5-yl)-benzaldehyde dimethyl ketal (2.28 g, 4.7 mmol reference example 97a) in THF (10 mL) is added hydrochloric acid (10 mL, 2M). The resulting mixture is stirred for 1 h. This mixture is concentrated to about half its original volume under reduced pressure. The solid is filtered then washed with water and ether to give the title compound (1.1 g) as a white solid. 1H NMR (DMSO) δ 7.88 (d, J=8 Hz, 2H), 7.95 (d, J=8 Hz, 2H), 8.79 (s, 2H), 9.99 (s, 1H).

Workup

  1. concentrationThis mixture is concentrated to about half its original volume under reduced pressure
  2. filtrationThe solid is filtered
  3. washthen washed with water and ether

Sources & evidence

ORD record
ord-03506ae669874a849c288b0ee982c14a
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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