3-Chloro-1-propanol → 4-Amino-2-(3-hydroxypropylthio)pyrimidine

HRID 544571Notes

Reaction equation

HRID 544571 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[S:3].[OH-].[Na+].Cl[CH2:12][CH2:13][CH2:14][OH:15]>O>[NH2:6][C:5]1[CH:7]=[CH:8][N:1]=[C:2]([S:3][CH2:12][CH2:13][CH2:14][OH:15])[N:4]=1

Participants

5

Reactant 3

HCID 123133-Chloro-1-propanolHCID 14798Sodium HydroxideHCID 178507915HCID 178507915, compound

Product 1

HCID 204582564-Amino-2-(3-hydroxypropylthio)pyrimidineYield 117%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-thiocytosine (0.88 g.), sodium hydroxide (0.32 g.), water (5 ml.) and 3-chloropropanol (0.8 g.) was heated at 90° for 1 hour and then cooled. The mixture was extracted with EtOAc and the extract dried and then evaporated to dryness to give 4-amino-2-(3-hydroxypropylthio)pyrimidine (1.5 g.) which was used without further purification.

Workup

  1. temperaturewas heated at 90° for 1 hour
  2. temperaturecooled
  3. extractionThe mixture was extracted with EtOAc
  4. customthe extract dried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-ddb1946689234fe3a92dcf7409f385c0
Source dataset
uspto-grants-1984_05
Patent number
US04451463

Reaction notes

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