Benzyl Alcohol → HCID 18470471, compound

HRID 2228920Notes

Reaction equation

HRID 2228920 reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].COC1N=C([N:19]2[C:24](=[O:25])[CH:23]=[CH:22][NH:21][C:20]2=[S:26])C=CN=1.C[N:28]([CH3:31])[CH:29]=O>>[CH2:1]([O:8][C:29]1[N:19]=[CH:24][C:23]([CH2:22][C:23]2[C:24](=[O:25])[NH:19][C:20](=[S:26])[NH:21][CH:22]=2)=[CH:31][N:28]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 244Benzyl AlcoholHCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 86758330HCID 86758330, compound

Product 1

HCID 18470471HCID 18470471, compound

Conditions

Temperature
80 °C

Procedure

To a solution of benzyl alcohol (20 ml) in dry dimethylformamide (20 ml) was added sodium hydride ((60% in oil) 2.3 g) over 0.5 h under argon. A slurry of 2-methoxypyrimidyl thiouracil (3.6 g) in dry dimethylformamide (10 ml) was added in one portion and the solution heated to 80° C. for 2.5 h. After cooling, the solvent was removed under reduced pressure and the residue partitioned between diethyl ether and water. The aqueous layer was washed with further diethyl ether and then acidified to pH4 with glacial acetic acid. The solid so formed was filtered, washed with water and diethyl ether and dried in vacuo to give the desired material. 1H-NMR (d6-DMSO) δ 3.49 (2H, s), 5.36 (2H, s), 7.2-7.5 (6H, m), 8.50 (2H, s); MS (APCI+) found (M+1)=327; C16H14N4O2S requires 326.

Workup

  1. temperatureAfter cooling
  2. customthe solvent was removed under reduced pressure
  3. customthe residue partitioned between diethyl ether and water
  4. washThe aqueous layer was washed with further diethyl ether
  5. customThe solid so formed
  6. filtrationwas filtered
  7. washwashed with water and diethyl ether
  8. customdried in vacuo

Sources & evidence

ORD record
ord-a2be7bed01364cc3acc04d0151c4fa10
Source dataset
uspto-grants-2002_07
Patent number
US06417192B1

Reaction notes

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