Hydrochloric Acid → HCID 68283326, compound

HRID 624059Notes

Reaction equation

HRID 624059 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([CH2:11][CH2:12][C:13](OC)=[O:14])[N:4]=1.[CH2:17]([O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22]([CH2:28][CH2:29][C:30](OC)=[O:31])[N:21]=1)[CH3:18].CC(C[AlH]CC(C)C)C.Cl>C1COCC1.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([CH2:11][CH2:12][CH2:13][OH:14])[N:4]=1.[CH2:17]([O:19][C:20]1[CH:25]=[C:24]([O:26][CH3:27])[N:23]=[C:22]([CH2:28][CH2:29][CH2:30][OH:31])[N:21]=1)[CH3:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 4252883HCID 4252883, compoundHCID 68283086HCID 68283086, compound

Product 2

HCID 68283326HCID 68283326, compoundHCID 68283390HCID 68283390, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of a mixture of methyl 3-(4,6-dimethoxypyrimidin-2-yl)propanoate and methyl 3-(4-ethoxy-6-methoxypyrimidin-2-yl)propanoate (1.71 g, 7.56 mmol) in THF (25 mL), DiBAL-H (1 M in THF, 23.0 mL, 23.0 mmol) was added at 0° C. After stirring for 40 min at 0° C., the reaction mixture was allowed to warm to rt, then diluted with DCM and acidified to pH 1 with 2 N aq. HCl-solution (50 mL). The org. layer was separated and the aq. layer was extracted with DCM (2×), then the aq. layer was bascified with aq. NaHCO3-solution and extracted with DCM (2×). The combined org. layers were dried (MgSO4), filtered and the solvent was removed under reduced pressure. Purification by prep. HPLC (basic) yielded 3-(4,6-dimethoxypyrimidin-2-yl)propan-1-ol and 3-(4-ethoxy-6-methoxypyrimidin-2-yl)propan-1-ol as yellow oils. 3-(4,6-dimethoxypyrimidin-2-yl)propan-1-ol: LC-MS conditions B: tR=0.43 min, [M+H]+=199.10. 3-(4-ethoxy-6-methoxypyrimidin-2-yl)propan-1-ol: LC-MS conditions B: tR=0.50 min, [M+H]+=213.13.

Workup

  1. additionwas added at 0° C
  2. temperatureto warm to rt
  3. customlayer was separated
  4. extractionthe aq. layer was extracted with DCM (2×)
  5. extractionextracted with DCM (2×)
  6. dry with materiallayers were dried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was removed under reduced pressure
  9. customPurification by prep

Sources & evidence

ORD record
ord-cfa378d89c2d4b79a0472a2eb4bf0cf7
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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