Hexadecylamine → Ethyl 2-hexadecylamino-5-pyrimidinecarboxylate

HRID 850976Notes

Reaction equation

HRID 850976 reaction equation
CS[C:3]1[N:8]=[CH:7][C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][N:4]=1.[CH2:14]([NH2:30])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].CN(C)P(N(C)C)(N(C)C)=O>O>[CH2:14]([NH:30][C:3]1[N:8]=[CH:7][C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:5][N:4]=1)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 8926HexadecylamineHCID 12679HexamethylphosphoramideHCID 10442716Ethyl 2-(methylthio)pyrimidine-5-carboxylate

Product 1

HCID 20503635Ethyl 2-hexadecylamino-5-pyrimidinecarboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.0 g of ethyl 2-methylthio-5-pyrimidinecarboxylate, 3.0 g. of hexadecylamine, and 20 ml. of hexamethylphosphoramide is heated at 110° C. for 10 hours, allowed to cool, and diluted with water. Filtration affords a solid which is crystallized from hexane to yield ethyl 2-hexadecylamino-5-pyrimidinecarboxylate as a tan solid.

Workup

  1. temperatureto cool
  2. filtrationFiltration
  3. customaffords a solid which
  4. customis crystallized from hexane

Sources & evidence

ORD record
ord-985a279069fe4e5aa1e33147ff8edd81
Source dataset
uspto-grants-1983_05
Patent number
US04382143

Reaction notes

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