Bis(2-chloroethyl)amine → 2,4-Diamino-6-(bis-2-chloroethyl)aminomethylpteridine

HRID 620143Notes

Reaction equation

HRID 620143 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[N:5][CH:6]=[C:7]([CH2:13]Br)[N:8]=2)[N:3]=1.[Cl:15][CH2:16][CH2:17][NH:18][CH2:19][CH2:20][Cl:21]>CN(C)C(=O)C>[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[N:5][CH:6]=[C:7]([CH2:13][N:18]([CH2:19][CH2:20][Cl:21])[CH2:17][CH2:16][Cl:15])[N:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 9533Bis(2-chloroethyl)amineHCID 4293426-Bromomethyl-2,4-pteridinediamine

Product 1

HCID 1250092,4-Diamino-6-(bis-2-chloroethyl)aminomethylpteridine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a stirred solution of 2.4 g (9.4 mmol) of 2,4-diamino-6-(bromomethyl)pteridine in 50 ml of N,N-dimethylacetamide was added 6 g (0.04 mol) of bis-(2-chloroethyl)amine, and the mixture was stirred at 50°-55° C. for 5 hours and then for 18 hours at room temperature. After filtering from a small amount of dark insoluble matter, the filtrate was diluted with 200 ml of water whereupon 2,4-diamino-6-bis(2-chloroethyl)-aminomethylpteridine separated as a light tan solid which was filtered, washed thoroughly with water and air dried; yield, 0.92 g (31%).

Workup

  1. waitfor 18 hours at room temperature
  2. filtrationAfter filtering from a small amount of dark insoluble matter
  3. additionthe filtrate was diluted with 200 ml of water whereupon 2,4-diamino-6-bis(2-chloroethyl)-aminomethylpteridine
  4. customseparated as a light tan solid which
  5. filtrationwas filtered
  6. washwashed thoroughly with water and air
  7. customdried
  8. customyield

Sources & evidence

ORD record
ord-2699f98468f4421da8ec6bda25dd99dc
Source dataset
uspto-grants-1989_04
Patent number
US04820706

Reaction notes

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