4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 59199967, compound

HRID 2382053Notes

Reaction equation

HRID 2382053 reaction equation
[CH3:1][C:2]1[C:7]([C:8]([OH:10])=O)=[CH:6][N:5]=[C:4]([C:11]2[N:16]=[CH:15][CH:14]=[CH:13][N:12]=2)[N:3]=1.[NH2:17][N:18]1[C:26]2[C:21](=[CH:22][C:23]([F:27])=[CH:24][CH:25]=2)[C:20]([CH2:28][CH2:29][C:30]([CH3:33])([OH:32])[CH3:31])=[CH:19]1.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CN(C=O)C.C([O-])([O-])=O.[Na+].[Na+]>[F:27][C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][CH:24]=1)[N:18]([NH:17][C:8]([C:7]1[C:2]([CH3:1])=[N:3][C:4]([C:11]3[N:16]=[CH:15][CH:14]=[CH:13][N:12]=3)=[N:5][CH:6]=1)=[O:10])[CH:19]=[C:20]2[CH2:28][CH2:29][C:30]([OH:32])([CH3:31])[CH3:33]

Participants

6

Reactant 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 616999854-Methyl-2-(pyrimidin-2-yl)pyrimidine-5-carboxylic acidHCID 685521584-(1-amino-5-fluoro-1H-indol-3-yl)-2-methyl-butan-2-ol

Product 1

HCID 59199967HCID 59199967, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 4-methyl-[2,2′]bipyrimidinyl-5-carboxylic acid (300 mg, 1.38 mmol) and 4-(1-amino-5-fluoro-1H-indol-3-yl)-2-methyl-butan-2-ol (325 mg, 1.38 mmol) in DMF (5 mL) is stirred at 50° C. for 1 h. The mixture is treated with DMTMM (380 mg, 1.38 mmol) and stirred at 50° C. for 2 h. The mixture is diluted with saturated aqueous Na2CO3 (50 mL), and extracted with EtOAc (3×50 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo. The residue is purified by silica gel chromatography eluting with 0%-7% MeOH in DCM to afford 4-methyl-[2,2′]bipyrimidinyl-5-carboxylic acid [5-fluoro-3-(3-hydroxy-3-methyl-butyl)-indol-1-yl]-amide (200 mg, 33%). MS: 435 (M+H); 1H NMR (300 MHz, CD3OD): δ 9.26 (s, 1H), 9.09 (d, 2H), 7.70 (t, 1H), 7.29 (m, 2H), 7.22 (s, 1H), 7.01 (m, 1H), 2.90 (s, 3H), 2.82 (m, 2H), 1.91 (m, 2H), 1.31 (s, 6H).

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. dry with materialThe combined organic layer is dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by silica gel chromatography
  6. washeluting with 0%-7% MeOH in DCM

Sources & evidence

ORD record
ord-c9bb765e75cc49e1b4fd937cdb2f500f
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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