HCID 67238653, compound → HCID 86654718, compound

HRID 711489Notes

Reaction equation

HRID 711489 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[C:5]([O:9][C:10]([NH:12][C@H:13]1[CH2:18][CH2:17][CH2:16][CH2:15][C@H:14]1[NH:19][C:20]1[N:25]=[C:24]([C:26]#[N:27])[C:23]([C:28](OC)=[O:29])=[C:22]([NH:32][C:33]2[CH:34]=[C:35]([CH3:39])[CH:36]=[CH:37][CH:38]=2)[N:21]=1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>CCOCC.CCOC(C)=O>[O:29]=[C:28]1[C:23]2[C:22]([NH:32][C:33]3[CH:34]=[C:35]([CH3:39])[CH:36]=[CH:37][CH:38]=3)=[N:21][C:20]([NH:19][C@@H:14]3[CH2:15][CH2:16][CH2:17][CH2:18][C@@H:13]3[NH:12][C:10](=[O:11])[O:9][C:5]([CH3:8])([CH3:6])[CH3:7])=[N:25][C:24]=2[C:26]2([CH2:2][CH2:1]2)[NH:27]1

Participants

5

Reactant 2

HCID 67238653HCID 67238653, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 86654718HCID 86654718, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethylmagnesium bromide (0.069 mL, 0.208 mmol) was added at RT to a solution of methyl 2-((1R,2S)-2-(tert-butoxycarbonylamino)cyclohexylamino)-4-cyano-6-(m-tolylamino)pyrimidine-5-carboxylate (50 mg, 0.104 mmol) and tetraisopropylorthotitanate (0.091 mL, 0.312 mmol) in Et2O (5 mL). The reaction mixture was stirred at RT for 20 h and was subsequently diluted with EtOAc. The organic phase was washed with saturated aq NaHCO3, brine and water, was dried then concentrated to give a pink residue, which was purified by reverse phase preparative HPLC. The fractions were collected and concentrated to a residue, which was used in next step. [M+H] calc'd for C26H34N6O3, 479. found, 479.

Workup

  1. washThe organic phase was washed with saturated aq NaHCO3, brine and water
  2. customwas dried
  3. concentrationthen concentrated
  4. customto give a pink residue, which
  5. customwas purified by reverse phase preparative HPLC
  6. customThe fractions were collected
  7. concentrationconcentrated to a residue, which

Sources & evidence

ORD record
ord-2c8f50eb8c3a4f5da0ee46a9520a99f7
Source dataset
uspto-grants-2015_11
Patent number
US09181255B2

Reaction notes

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