Ethanol → HCID 54136945, compound

HRID 1579318Notes

Reaction equation

HRID 1579318 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH3:18])[C:13]([C:19](=[O:25])[CH2:20][S:21]([CH3:24])(=[O:23])=[O:22])=[C:12]([O:26][CH2:27][CH3:28])[CH:11]=2)=[CH:4][N:3]=1.C(O)C.[BH4-].[Na+]>O>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:11]=[C:12]([O:26][CH2:27][CH3:28])[C:13]([CH:19]([OH:25])[CH2:20][S:21]([CH3:24])(=[O:22])=[O:23])=[C:14]([O:16][CH2:17][CH3:18])[CH:15]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 232770301-[4-[(2,4-Diaminopyrimidin-5-yl)methyl]-2,6-diethoxyphenyl]-2-methylsulfonylethanone

Product 1

HCID 54136945HCID 54136945, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a suspension of 1 g. of 4'-[(2,4-diamino-5-pyrimidinyl)-methyl]-2',6'-diethoxy-2-(methylsulfonyl)-acetophenone in a mixture of 25 ml. of ethanol and 10 ml. of water there is added portionwise with stirring over a period of 30 minutes 500 mg. of sodium borohydride. First the solution becomes clear, and after an additional 30 minutes of stirring, there crystallizes 4-[(2,4-diamino-5-pyrimidinyl)-methyl]-2,6-diethoxy-α-[(methylsulfonyl)-methyl]-benzyl alcohol, having a m.p. of 205°-206° after recrystallization from methanol.

Workup

  1. additionTo a suspension of 1 g
  2. stirringafter an additional 30 minutes of stirring
  3. customthere crystallizes 4-[(2,4-diamino-5-pyrimidinyl)-methyl]-2,6-diethoxy-α-[(methylsulfonyl)-methyl]-benzyl alcohol
  4. customafter recrystallization from methanol

Sources & evidence

ORD record
ord-ca1ebeaa6d5c4cbe9aecf76fbff12a4b
Source dataset
uspto-grants-1976_01
Patent number
US03931181

Reaction notes

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