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Trimethylaluminum → HCID 178489784, compound

HRID 1092177
Notes
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Reaction equation

HRID 1092177 reaction equation
C[Al](C)C.[CH:5]1([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]3[N:20]=[CH:19][C:18]([C:21]([O:23]C)=O)=[CH:17][N:16]=3)[CH2:10][CH2:9]2)[CH2:7][CH2:6]1.[CH3:25][O:26][C:27]1[CH:28]=[C:29]([CH2:35][CH2:36][C:37]2[CH:38]=[C:39]([NH2:42])[NH:40][N:41]=2)[CH:30]=[C:31]([O:33][CH3:34])[CH:32]=1>C1(C)C=CC=CC=1>[CH:5]1([N:8]2[CH2:14][CH2:13][CH2:12][N:11]([C:15]3[N:16]=[CH:17][C:18]([C:21]([NH:42][C:39]4[NH:40][N:41]=[C:37]([CH2:36][CH2:35][C:29]5[CH:30]=[C:31]([O:33][CH3:34])[CH:32]=[C:27]([O:26][CH3:25])[CH:28]=5)[CH:38]=4)=[O:23])=[CH:19][N:20]=3)[CH2:10][CH2:9]2)[CH2:6][CH2:7]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 16682925TrimethylaluminumHCID 66589974Methyl 2-(4-cyclopropyl-1,4-diazepan-1-yl)pyrimidine-5-carboxylateHCID 178489815HCID 178489815, compound

Product 1

HCID 178489784HCID 178489784, compoundYield 1.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Trimethylaluminium (1.402 ml, 2.80 mmol) was added dropwise to a stirred suspension of methyl 2-(4-cyclopropyl-1,4-diazepan-1-yl)pyrimidine-5-carboxylate (310 mg, 1.12 mmol) and 5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-amine (277 mg, 1.12 mmol) in toluene (5.61 ml) at 25° C. The resulting solution was stirred at 60° C. for 18 h. The cooled reaction mixture was quenched into methanol (50 mL) and treated with HCl (2M aqueous solution, to pH7 or lower) and purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH and evaporated to dryness to afford impure product. The crude product was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (8.00 mg, 1%) as a cream solid. Some impure fractions were combined and concentrated to dryness and purified by crystallisation from MeCN to afford the title compound (51 mg, 9%) as a cream solid.

Workup

  1. customThe cooled reaction mixture
  2. customwas quenched into methanol (50 mL)
  3. additiontreated with HCl (2M aqueous solution, to pH7 or lower)
  4. custompurified by ion exchange chromatography
  5. washThe desired product was eluted from the column
  6. customevaporated to dryness
  7. customto afford impure product
  8. customThe crude product was purified by preparative HPLC
  9. additionFractions containing the desired compound
  10. customwere evaporated to dryness

Sources & evidence

ORD record
ord-12cbb3cd4585403b807c875233dcf2a2
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08129391B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes