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Dimethylformamide → (E)-Ethyl 3-(2-amino-4-(ethylamino)-6-methylpyrimidin-5-yl)acrylate

HRID 1893895
Notes
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Reaction equation

HRID 1893895 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[C:7](I)[CH:6]=[C:5]([NH:10][CH2:11][CH3:12])[N:4]=1.[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[CH:14]=[CH2:15].[CH2:20](N(CC)CC)C.CN(C=O)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(C)=O>[NH2:2][C:3]1[N:4]=[C:5]([NH:10][CH2:11][CH3:12])[C:6](/[CH:15]=[CH:14]/[C:13]([O:17][CH2:18][CH3:19])=[O:16])=[C:7]([CH3:20])[N:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 866284152-Amino-6-ethylamino-4-iodopyrimidine hydrochloride

Product 1

HCID 57606983(E)-Ethyl 3-(2-amino-4-(ethylamino)-6-methylpyrimidin-5-yl)acrylateYield 67%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 180AcetoneSolvent

Conditions

Temperature
95 °C

Procedure

To a three-neck round bottom flask equipped with over-head mechanic stirrer were added 2-amino-6-ethylamino-4-iodopyrimidine hydrochloride (188.5 g, 0.60 mol), ethyl acrylate (221 mL, 2.0 mol), triethylamine (285 mL, 2.0 mol), DMF (1.3 L), and tetrakis(triphenylphosphine)palladium(0) (Pd(PPh3)4, 31.3 g, 0.027 mol). The reaction mixture was heated to 95° C. and stirred for 3 h (monitored by LC/MC). After reaction completion, the reaction mixture was evaporated about to 1/10 of original volume and partitioned with 500 mL of ethyl acetate and 1000 mL of water. The aqueous layer was extracted with ethyl acetate 5 times. (E)-Ethyl 3-(2-amino-4-(ethylamino)-6-methylpyrimidin-5-yl)acrylate (100 g, 67% yield) was obtained by recrystallization from acetone after evaporation of ethyl acetate. 1H NMR (400 MHz, CD3OD) δ 7.48 (dd, J1=16.0 Hz, J2=4.0 Hz, 1H), 6.20 (dd, J1=16 Hz, J2=4 Hz, 1H), 4.25 (q, J=7.2 Hz, 2H), 3.51 (q, J=7.6 Hz, 2H), 2.39 (s, 3H), 1.3 (t, J=7.2 Hz, 3H), 1.2 (t, J=7.6 Hz, 3H). MS (EI) for C12H18N4O2: 251.3 (MH+).

Workup

  1. customTo a three-neck round bottom flask equipped with over-head mechanic stirrer
  2. customAfter reaction completion
  3. customthe reaction mixture was evaporated about to 1/10 of original volume
  4. custompartitioned with 500 mL of ethyl acetate and 1000 mL of water
  5. extractionThe aqueous layer was extracted with ethyl acetate 5 times

Sources & evidence

ORD record
ord-f78b1c5b51b4402399ba20062634bac1
Source dataset
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08513266B2

Reaction notes

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