Dimethylformamide → 4-Amino-2-[(4-chlorophenoxy)methyl]pteridine

HRID 326850

Reaction equation

HRID 326850 reaction equation
[NH2:1][C:2]1[C:3]([C:8]#[N:9])=[N:4][CH:5]=[CH:6][N:7]=1.[Cl:10][C:11]1[CH:21]=[CH:20][C:14]([O:15][CH2:16][C:17](N)=[NH:18])=[CH:13][CH:12]=1.CN(C)C=O>C(O)C>[NH2:9][C:8]1[C:3]2[C:2](=[N:7][CH:6]=[CH:5][N:4]=2)[N:1]=[C:17]([CH2:16][O:15][C:14]2[CH:20]=[CH:21][C:11]([Cl:10])=[CH:12][CH:13]=2)[N:18]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 8176993-Aminopyrazine-2-carbonitrileHCID 27357872-(4-Chlorophenoxy)ethanimidamide

Product 1

HCID 107557494-Amino-2-[(4-chlorophenoxy)methyl]pteridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Obtained using the procedure described in section c of Example 2, starting with 10.7 g (0.089 mole) of 3-amino-2-pyrazinecarbonitrile and 24.5 g (0.133 mole) of 2-(4-chlorophenoxy)acetamidine [prepared according to C. Djerassi and C. R. Scholz, U.S. Pat. No. 2,517,468; C.A. 1951, 45, 661f] in 320 ml of absolute ethanol. Refluxing time: 7 hours. Yld: 21.5 g (84%), m.p. 246°-248° C. (N,N-dimethylformamide).

Workup

  1. customObtained
  2. customprepared
  3. temperatureRefluxing time
  4. custom7 hours

Sources & evidence

ORD record
ord-80961a04363848518e55b6a7f3125464
Source dataset
uspto-grants-1993_12
Patent number
US05270465

Linked notes

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