Water → HCID 178508880, compound

HRID 1903300Notes

Reaction equation

HRID 1903300 reaction equation
[NH2:1][C:2]1[N:3]=[C:4](Cl)[C:5]2[S:11][CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=1.[O:13]=C1CCCSC1C(OCC)=O.[Na].O>C(O)C.C(O)(=O)C>[NH2:1][C:2]1[N:3]=[C:4]([OH:13])[C:5]2[S:11][CH2:10][CH2:9][CH2:8][C:6]=2[N:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5360545SodiumHCID 12269128ethyl 3-oxotetrahydro-2H-thiopyran-2-carboxylateHCID 133071552-amino-4-chloro-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine

Product 1

HCID 178508880HCID 178508880, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

The starting material, 2-amino-4-chloro-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine, was prepared in the following manner. 56.4 g of ethyl 3-oxotetrahydrothiopyran-2-carboxylate was added to a solution of 6.9 g of sodium metal in 300 ml of ethanol at room temperature while stirring. After stirring overnight, water was added to the mixture, and the mixture was rendered acidic with acetic acid. The precipitated crystals were filtered, washed with water and then with a small amount of isopropyl alcohol and air-dried to obtain 45 g of 2-amino-4-hydroxy-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine as colorless needles having a melting point above 300° C.

Workup

  1. stirringAfter stirring overnight
  2. filtrationThe precipitated crystals were filtered
  3. washwashed with water
  4. dry with materialwith a small amount of isopropyl alcohol and air-dried

Sources & evidence

ORD record
ord-a897ac55a1974b40a46ab67e2c90615a
Source dataset
uspto-grants-1984_03
Patent number
US04435566

Reaction notes

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