Phosphoric Acid → HCID 22349861, compound

HRID 896227Notes

Reaction equation

HRID 896227 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[C:7]([N:15]2[CH2:20][CH2:19][N:18]([CH2:21][CH2:22][CH2:23][S:24][C:25]3[N:29]([CH3:30])[C:28]([CH3:31])=[N:27][N:26]=3)[CH2:17][CH2:16]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH:32][P:33]([OH:36])([OH:35])=[O:34].C(OC(C)C)(=O)C>C(O)(C)C.O>[P:33]([OH:36])([OH:35])([OH:34])=[O:32].[P:33]([OH:36])([OH:35])([OH:34])=[O:32].[P:33]([OH:36])([OH:35])([OH:34])=[O:32].[P:33]([OH:36])([OH:35])([OH:34])=[O:32].[C:1]([C:5]1[N:10]=[C:9]([C:11]([CH3:13])([CH3:12])[CH3:14])[CH:8]=[C:7]([N:15]2[CH2:16][CH2:17][N:18]([CH2:21][CH2:22][CH2:23][S:24][C:25]3[N:29]([CH3:30])[C:28]([CH3:31])=[N:27][N:26]=3)[CH2:19][CH2:20]2)[N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 1004Phosphoric AcidHCID 7915Isopropyl AcetateHCID 114307322-tert-Butyl-4-(4-(3-((4-methyl-5-methyl-4H-(1,2,4)triazol-3-yl)sulfanyl)propyl)piperazin-1-yl)-6-tert-butylpyrimidine

Product 1

HCID 22349861HCID 22349861, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 2,4-Di-tert-butyl-6-{4-[3-(4,5-dimethyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propyl]-piperazin-1-yl}-pyrimidine (7.47 g, 16.8 mmol) in isopropanol (74.70 g) was added a H3PO4 solution in water (8.23 g H3PO4 (85%) in 28.89 g of water). The solution was heated to 60° C. and seeded with a slurry of the tetra-phosphate salt (143 mg) in isopropanol (1.41 g). The mixture was slowly cooled to 20° C. and isopropyl acetate (103.99 g) was charged. The solid was filtered off and washed (2×28 g) with a solution of isopropanol/isopropyl acetate (1:1). The solid was dried in a vacuum oven at 72° C. to afford 13.1 g (96.3% yield) of 2,4-di-tert-butyl-6-{4-[3-(4,5-dimethyl-4H-[1,2,4]triazol-3-ylsulfanyl)-propyl]-piperazin-1-yl}-pyrimidine tetra-phosphate salt as a white solid.

Workup

  1. temperatureThe mixture was slowly cooled to 20° C.
  2. filtrationThe solid was filtered off
  3. washwashed (2×28 g) with a solution of isopropanol/isopropyl acetate (1:1)
  4. customThe solid was dried in a vacuum oven at 72° C.

Sources & evidence

ORD record
ord-645f2b01218443c88ef02a473c229d64
Source dataset
uspto-grants-2005_07
Patent number
US06919342B2

Reaction notes

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