Methylamine → HCID 131714288, compound

HRID 371459Notes

Reaction equation

HRID 371459 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:23]=[CH:22][C:18]([C:19](O)=[O:20])=[CH:17][CH:16]=3)[CH2:11][CH2:10]2)=[C:4]([CH3:24])[N:3]=1.P([C:33]#[N:34])(=O)(OCC)OCC.C(N(CC)CC)C.CN>CN(C)C=O>[OH2:20].[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[CH:16]=[CH:17][C:18]([C:19]([NH:34][CH3:33])=[O:20])=[CH:22][CH:23]=3)[CH2:13][CH2:14]2)=[C:4]([CH3:24])[N:3]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 9840389HCID 9840389, compound

Product 1

HCID 131714288HCID 131714288, compoundYield 1,043.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.6 g (8.0 mmole) of 4-[4-(2,4-diamino-6-methyl-5-pyrimidinyl)-1-piperazinyl]benzoic acid, 4.3 g (26.4 mmole) of diethyl phosphorocyanidate and 3.7 ml (26.4 mmole) of triethyl amine in 500 ml of N,N-dimethylformamide (dried over 4 Å molecular sieves overnight) was stirred at room temperature for five hours. Gaseous monomethylamine was passed into the suspension for one hour. The suspension initially became a clear solution and then a precipitate formed. The solvent was removed under high vacuum (0.1 mm, dry ice-2-propanol trap). The gummy residue was dissolved in 200 ml of ice water and neutralized to pH 7 by adding saturated sodium carbonate solution. The solid was collected and recrystallized from N,N-dimethylformamide to afford 15 g of the product as an off-white solid, mp 305° C. (with decomposition).

Workup

  1. customa precipitate formed
  2. customThe solvent was removed under high vacuum (0.1 mm, dry ice-2-propanol trap)
  3. dissolutionThe gummy residue was dissolved in 200 ml of ice water and neutralized to pH 7
  4. additionby adding saturated sodium carbonate solution
  5. customThe solid was collected
  6. customrecrystallized from N,N-dimethylformamide

Sources & evidence

ORD record
ord-efece36363824687851f76dc818a4414
Source dataset
uspto-grants-1985_07
Patent number
US04532240

Reaction notes

Loading…