Diisopropylethylamine → N4-(5-Cyclopropyl-1H-pyrazol-3-yl)-N2-((3-methyl-1H-indol-4-yl)methyl)pyrimidine-2,4-diamine

HRID 475269Notes

Reaction equation

HRID 475269 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[NH:13][N:12]=[C:11]([CH:14]3[CH2:16][CH2:15]3)[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][C:25]=2[CH2:27][NH2:28])[NH:20][CH:19]=1.CCN(C(C)C)C(C)C>CC(O)C>[CH:14]1([C:11]2[NH:12][N:13]=[C:9]([NH:8][C:6]3[CH:5]=[CH:4][N:3]=[C:2]([NH:28][CH2:27][C:25]4[CH:24]=[CH:23][CH:22]=[C:21]5[C:26]=4[C:18]([CH3:17])=[CH:19][NH:20]5)[N:7]=3)[CH:10]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 83815702(3-methyl-1H-indol-4-yl)methanamineHCID 178478345HCID 178478345, compound

Product 1

HCID 86694747N4-(5-Cyclopropyl-1H-pyrazol-3-yl)-N2-((3-methyl-1H-indol-4-yl)methyl)pyrimidine-2,4-diamine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
120 °C

Procedure

A tube was charged with 53 (200 mg, 0.85 mmol), 234 (181 mg, 1.13 mmol), DIPEA (0.2 mL) and IPA (2 mL), degassed, sealed and heated at 120° C. overnight. The solvent was concentrated to dryness in vacuo. The residue was purified by preparative HPLC to afford 80 mg (26%) of I-92 as white solid.

Workup

  1. customdegassed
  2. customsealed
  3. concentrationThe solvent was concentrated to dryness in vacuo
  4. customThe residue was purified by preparative HPLC
  5. customto afford 80 mg (26%) of I-92 as white solid

Sources & evidence

ORD record
ord-478e5b2bf3114494b37dbee024885d9e
Source dataset
uspto-grants-2014_01
Patent number
US08637537B2

Reaction notes

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