Hydrochloric Acid → 5-(4-phenoxyphenyl)-N4-(2-azaspiro[3.3]heptan-6-yl)pyrimidine-4,6-diamine

HRID 1522097Notes

Reaction equation

HRID 1522097 reaction equation
C(OC([N:8]1[CH2:11][C:10]2([CH2:14][CH:13]([NH:15][C:16]3[C:21]([C:22]4[CH:27]=[CH:26][C:25]([O:28][C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)=[CH:24][CH:23]=4)=[C:20]([NH2:35])[N:19]=[CH:18][N:17]=3)[CH2:12]2)[CH2:9]1)=O)(C)(C)C.Cl>CO>[O:28]([C:25]1[CH:24]=[CH:23][C:22]([C:21]2[C:16]([NH:15][CH:13]3[CH2:14][C:10]4([CH2:9][NH:8][CH2:11]4)[CH2:12]3)=[N:17][CH:18]=[N:19][C:20]=2[NH2:35])=[CH:27][CH:26]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71113289Tert-butyl 6-((6-amino-5-(4-phenoxyphenyl)pyrimidin-4-yl)amino)-2-azaspiro[3.3]heptane-2-carboxylate

Product 1

HCID 711132175-(4-phenoxyphenyl)-N4-(2-azaspiro[3.3]heptan-6-yl)pyrimidine-4,6-diamineYield 38.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a round bottom flask containing 6-[6-amino-5-(4-phenoxy-phenyl)-pyrimidin-4-ylamino]-2-aza-spiro[3.3]heptane-2-carboxylic acid tert-butyl ester (167.23 mg; 0.35 mmol; 1.00 eq.) in methanol (5.00 ml) was added hydrogen chloride (1.80 ml; 3.53 mmol; 10.00 eq.). The reaction was stirred for 16 h before it was concentrated and purified by HPLC. The fractions containing the desired product were lyophilized to afford the title compound as a white solid (50.3 mg, 34%). HPLC purity: 95%. MS: m/z=374[M+H]+. 1H NMR (CD3OD) δ 8.25 (s, 1H), 7.10-7.44 (m, 8H), 4.60 (m, 1H), 4.20 (s, 2H), 4.01 (s, 2H), 2.69 (m, 2H), 2.32 (m, 2H).

Workup

  1. concentrationwas concentrated
  2. custompurified by HPLC
  3. additionThe fractions containing the desired product

Sources & evidence

ORD record
ord-8f910271b68647139b6fc9e9a4a39d09
Source dataset
uspto-grants-2015_07
Patent number
US09073947B2

Reaction notes

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