5-(4-(benzyloxy)-3-fluorophenyl)-2-(cyclopropylmethylamino)-3-methylpyrimidin-4(3H)-one → HCID 68518200, compound

HRID 2241241Notes

Reaction equation

HRID 2241241 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16](=[O:27])[N:17]([CH3:26])[C:18]([NH:21][CH2:22][CH:23]3[CH2:25][CH2:24]3)=[N:19][CH:20]=2)=[CH:11][C:10]=1[F:28])C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[CH:23]1([CH2:22][NH:21][C:18]2[N:17]([CH3:26])[C:16](=[O:27])[C:15]([C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([F:28])[CH:11]=3)=[CH:20][N:19]=2)[CH2:25][CH2:24]1

Participants

3

Reactant 1

HCID 685137375-(4-(benzyloxy)-3-fluorophenyl)-2-(cyclopropylmethylamino)-3-methylpyrimidin-4(3H)-one

Product 1

HCID 68518200HCID 68518200, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 5-(4-(benzyloxy)-3-fluorophenyl)-2-(cyclopropylmethylamino)-3-methylpyrimidin-4(3H)-one (0.128 g, 0.337 mmol) in TFA (2 mL) was stirred at 40° C. for 2 hours and 45 minutes. The reaction mixture was concentrated to dryness and then purified by flash column chromatography, eluting with 20:1 dichloromethane/MeOH. The desired product (0.080 g, 82%) was obtained as a colorless glassy solid. 1H NMR (400 MHz, DMSO-d6) δ 9.71 (s, 1H), 7.87 (s, 1H), 7.46 (dd, J=2.3, 13.7 Hz, 1H), 7.35 (t, J=5.3 Hz, 1H), 7.24 (dd, J=2.3, 8.4 Hz, 1H), 6.90 (dd, J=8.4, 9.6 Hz, 1H), 3.34 (s, 3H), 3.24 (t, J=6.2 Hz, 2H), 1.16 (m, 1H), 0.44 (m, 2H), 0.26 (m, 2H). LRMS (ESI pos) m/e 290 (M+1).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompurified by flash column chromatography
  3. washeluting with 20:1 dichloromethane/MeOH

Sources & evidence

ORD record
ord-02c2e1b2fb0d488e863ee473311728c2
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

Loading…