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4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 59200064, compound

HRID 2382134
Notes
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Reaction equation

HRID 2382134 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[N:12]=[C:11]([CH3:13])[C:10]([C:14]([OH:16])=O)=[CH:9][N:8]=1.[CH3:17][O:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([NH2:28])[CH:23]=[CH:22]2.C[N+]1(C2N=C(OC)N=C(OC)N=2)CCOCC1.[Cl-]>CN(C=O)C>[O:18]([C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[N:24]([NH:28][C:14]([C:10]1[C:11]([CH3:13])=[N:12][C:7]([C:2]3[N:1]=[CH:6][CH:5]=[CH:4][N:3]=3)=[N:8][CH:9]=1)=[O:16])[CH:23]=[CH:22]2)[CH3:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 10607077HCID 10607077, compoundHCID 616999854-Methyl-2-(pyrimidin-2-yl)pyrimidine-5-carboxylic acid

Product 1

HCID 59200064HCID 59200064, compoundYield 116.1%

Reagents, catalysts & solvents 1

HCID 6228Dimethylformamide
Solvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-pyrimidin-2-yl-4-methyl-pyrimidine-5-carboxylic acid (496 mg, 2.30 mmol) and 5-methoxy-indol-1-ylamine (0.98 mmol) in anhydrous DMF (10 mL) is stirred at 50° C. for 30 min. DMTMM (555 mg, 2.01 mmol) is added and stirred at 50° C. for an hour. DMF is evaporated off. The residue is mixed with water (40 mL) and stirred at rt for 20 minutes. The solid is collected by filtration, washed with water (3×5 mL) and dried in vacuum to afford 2-pyrimidin-2-yl-4-methyl-pyrimidine-5-carboxylic acid (5-methoxyl-indol-1-yl)-amide (410 mg) as a solid. MS: 361 (M+H); 1H NMR (300 MHz, CD3OD): δ 2.93(s, 3H), 4.84(s, 3H), 7.04(t, H), 6.50(d, H), 6.92(d, H), 7.14(s, H), 7.26-7.37(m, 2H), 7.72 (t, H), 9.09 (d, 2H), 9.27(s, H).

Workup

  1. customDMF is evaporated off
  2. additionThe residue is mixed with water (40 mL)
  3. stirringstirred at rt for 20 minutes
  4. filtrationThe solid is collected by filtration
  5. washwashed with water (3×5 mL)
  6. customdried in vacuum

Sources & evidence

ORD record
ord-51aa6561870849dc8e10483cf31405df
Source dataset
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08258130B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes