Triethylamine → N-(5-amino-6-oxo-3-pentyl-2-thioxo-1,2,3,6-tetrahydropyrimidin-4-yl)cyclobutanecarboxamide

HRID 1664538Notes

Reaction equation

HRID 1664538 reaction equation
[NH2:1][C:2]1[C:3](=[O:15])[NH:4][C:5](=[S:14])[N:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:7]=1[NH2:8].[CH:16]1([C:20](O)=[O:21])[CH2:19][CH2:18][CH2:17]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C=O)C.O>[NH2:1][C:2]1[C:3](=[O:15])[NH:4][C:5](=[S:14])[N:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:7]=1[NH:8][C:20]([CH:16]1[CH2:19][CH2:18][CH2:17]1)=[O:21]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 19494Cyclobutanecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 576002545,6-Diamino-1-pentyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

Product 1

HCID 57600174N-(5-amino-6-oxo-3-pentyl-2-thioxo-1,2,3,6-tetrahydropyrimidin-4-yl)cyclobutanecarboxamideYield 83.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The mixture of 5,6-diamino-1-pentyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (1060 mg, 0.00464 mol), cyclobutane carboxylic acid (0.55 g, 5.5 mmol), benzotriazol-1-yloxytris-(dimethylamino)phosphonium hexafluorophosphate (2.2 g, 5.1 mmol) and triethylamine (1.3 mL, 9.3 mmol) in DMF (20 mL) was stirred at room temperature for 4 hours. The mixture was diluted with water. The precipitate formed was filtered and dried to yield the desired product (1.20 g, 83.27%). LCMS calculated for C14H23N4O2S (M+H): 311.2. found 311.2.

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered
  3. customdried

Sources & evidence

ORD record
ord-8481327a4d5b4c13bd33b7de36989cb0
Source dataset
uspto-grants-2011_10
Patent number
US08039478B2

Reaction notes

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